smo_main (kewpie2)

Transcription

smo_main (kewpie2)

HETEROCYCLES, Vol. 82, No. 2, 2011
■ REVIEWS
917
Synthesis of Rhazinilam: A Comparative Review of
Forty Years of Synthetic Endeavors
Inga Kholod, Olivier Vallat, Ana-Maria Buciumas, and
Reinhard Neier*
O
NH
N
Rhazinilam
949
Total Synthesis
Retrosynthesis
Pyrrole
Natural Product
Development and Applications of an Oxazole-Forming
Reaction
O
R1
N
Jianmin Zhang,* Pierre-Yves Coqueron, and
Marco A. Ciufolini*
O
R2
R1
CO2R3
R1
Cl
O
N
Alkaloid
981
Oxazole
Organoaluminum Compound
Muscoride
CO2R3
N
H
N
CO2R3
NH2
CO2R3
Properties and Bioactivities of Peptoids Tagged with
Heterocycles
Me
R2
O
H
N
R1
N
H
O
Peptoid
Peptidomimetic
Heterocycle
Molecular Recognition
R2
O
O
H
N
Me
Me
R3
O
N
N
R1
peptide
Indole Chemistry for Combating Yellow Sand and
Desertification Directed towards Stopping Global
Warming
R3
peptoid
SOMRE Compounds
Root growth regulating and promoting activity
CHO
CHO
N
H
N
H
N
H
R
OH
R = Br, Cl, I, various substituent
SOMRE Compound
Plant Root Growth Promoter
2-Bromoindole-3-carbaldehyde
4-Alkynoic Acids in the Synthesis of Biologically
Important Tetrapyrroles
Peter A. Jacobi,* Harry L. Brielmann, Melanie Chiu,
Indranath Ghosh, Sheila I. Hauck, Sandra Lanz, Sam Leung,
Yongkai Li, Hui Liu, Franzisca Löwer, William G. O’Neal,
Douglas Pippin, Elizabeth Pollina, Benjamin A. Pratt,
Frédéric Robert, William P. Roberts, Carlos Tassa, and
Hui Wang
Gobi Desert
A
O
B
O
H
1
Bacteriochlorin
Corrin
Alkynoic Acid
Pd(0)-Coupling/Cyclization
Indole Chemistry
A
R
4-alkynoic acids
Chlorin
Me
N
O
N-Alkyloligoglycine
Masanori Somei*
1029
R2
Siphonazole
Irene Izzo, Chiara De Cola, and Francesco De Riccardis*
1007
H
N
O
R1
D
N
N
N
HN
B
C
corrins, etc.
1083
Further Application of the Multi-Template Approach for
Creation of Biological Response Modifiers: Discovery
of a New Class of Multifunctional Anti-Diabetic Agents
O
Kazunori Motoshima, Tomomi Noguchi-Yachide,
Minoru Ishikawa, Yuichi Hashimoto, and Kazuyuki Sugita*
O
N
O
O
NH
O
2'
4" R2
3'
N
3"
4'
R1
O
thalidomide (1) as a multi-template
Anti-Diabetic Agent
Metabolic Syndrome
Multi-Template
Thalidomide
Scaffold
■ COMMUNICATIONS
1103
Unexpected Formation of Dihydrobenzosilole Derivative
via the Intramolecular Cyclization in the Reaction of
Overcrowded Dichloromethylsilane with Aryllithium
Me3Si
Takahiro Sasamori,* Eiko Mieda, and Norihiro Tokitoh*
Tsi
SiH2
Me3Si
Silene
1113
Chlorocarbene
Dihydrobenzosilole
Intramolecular Cyclization
ArLi
CHCl2
SiMe3
Dis
Ar
OH
N
OBn
O
OH
LiHMDS
85%
(only isomer)
N
O
(+)-3-(Z)-dihydrorhodophytin
O
Intermolecular Amide Enolate Alkylation
Minoru Tamiya,* Futa Takada, Nobuhisa Isaka,
Nahoko Iimura, and Masaji Ishiguro*
Ring-Closing Metathesis
OTMS
H
H
H
H
Pd(OAc)2
(5 mol%)
O2 (28 atm)
DMSO/CH2Cl2
(1/1)
–15 °C
MeO
Medium-Sized Oxacycle
O
O
H
H
MeO
Steroid
Palladium Catalyzed Reaction
Beayer-Villiger Reaction
Oxygen
OBn
O
Cl
Br
Modification of D-Ring Moiety of Steroids !
A Novel Palladium Catalyzed Baeyer-Villiger
Type Rearrangement of Cyclic Silylenol Ether
Derivatives
Ar
Dis
Silicate
2) RCM
1119
SiMe3
SiH2
Tsi = C(SiMe3)3
Dis = CH(SiMe3)2
unexpected cyclization reaction
1) chlorination
(+)-3-(Z)-Dihydrorhodophytin
H
Si H + Tsi
O
Total Synthesis
Me3Si
CH2
Tsi
SiMe3
Concise Substrate-Controlled Asymmetric
Total Synthesis of (+)-3-(Z)-Dihydrorhodophytin
Byungsook Kim, Te-ik Sohn, Sanghee Kim,
Deukjoon Kim,* and Jongkook Lee
Me3Si
SiMe3
25%
Saegusa-Ito Oxidation
H
H
+
H
MeO
73%
H
O
1127
Asymmetric Synthesis of (+)-Machilin F by Unusual
Stereoselective Mitsunobu Reaction
Kenichi Harada, Naoko Kubo, Kazuma Tanabe,
Miwa Kubo, Tomoyuki Esumi, Hideaki Hioki, and
Yoshiyasu Fukuyama*
O
O
OH
OMe
Talaumidin
1133
Machilin F
Asymmetric Synthesis
Mitsunobu Reaction
O
O
OMe
machilin F
56%
Neurotrophic Activity
Unprecedented Synthesis of N,N-Divinylamines by
Tf2NH-Catalyzed Reaction of Ynamide with Ketimine
Naoya Shindoh, Yoshiji Takemoto,* and Kiyosei Takasu*
R1
EWG
N
Ar1
R2
Ynamide
Triflic Imide
Addition
Divinylamine
Ar2
N
+
1137
HO
DIAD, PPh3
CH2Cl2, rt
OH
RO
O
Mitsunobu-type
reaction
EWG Ar2
Tf2NH (cat.)
R1
Me
N
Ar1
N
R2
Catalytic Reaction
Hexamethyldisilazane-Promoted Sonogashira
Reaction of Polyfunctionalized N-Containing
Heterocycles
DMTrO
H
O
HO
O
Pd catalyst, CuI
+
Hal
HMDS-DMF
N
X
N
DMTrO
Masahiko Inouye,* Yasuhiro Doi, Junichi Azuchi,
Wataru Shirato, Junya Chiba, and Hajime Abe*
Y
RO
R = H or TMS
X
Y
Sonogashira Reaction
1143
Hexamethyldisilazane
Alkynyl C-Nucleoside
Pyridone
McMurry Coupling of Diformyldithienylacetylene:
Synthesis of [24]-, [36]-, and [48]Annulenes Composed
of Thiophene, Acetylene, and Ethylene Units
Bu-n
n-Bu
Masahiko Iyoda,* Pochi Huang, Tomohiko Nishiuchi,
Masayoshi Takase, and Tohru Nishinaga
Pyrimidine
S
OHC
Bu-n
n-Bu
n-Bu
Bu-n
S
CHO
1151
Annulene
S
S
Py, THF
S
S
n
n-Bu
Cyclic Oligothiophene
Twisted Structure
Bu-n
TiCl4, Zn
Bu-n
Bu-n
n-Bu
n = 1 [Z,Z-24!
!]
n = 2 [Z,Z,Z-36!
!]
n = 3 [E,Z,E,Z-48!
!]
n=1
McMurry Coupling Reaction
n-Bu
Dication Fromation
Synthesis of Antioxidant Flavonoid Derivatives
Emiko Yanase, Young P. Jang, and Koji Nakanishi*
OH
HO
O
OH
HO
OH
O
Antioxidant
Quercetin
O
HN
O
Caffeic Acid
O
MeO
Curcumin
OMe
O
O
quercetin
Age-Related Macular Degeneration (AMD)
O
OH
OH
OH
OH
O
OH
quercetin - curcumin conjugate
1157
Oxidation of Pyrrole-2-carboxylates with o-Chloranil
and Its Synthetic Application
Ryo Sakata, Ryoji Iwamoto, Shuhei Fujinami,
Yutaka Ukaji,* and Katsuhiko Inomata*
R1
R2
H
Oxidation
1163
Pyrrole-2-carboxylate
o-Chloranil
CO2Bu-tert
N
H
5-Methoxypyrrolin-2-one Derivative
[2,3] Wittig Rearrangement of "’-Hydroxyethyl
Bis-Allylic Ethers: Highly Regiospecific Entry to
Singly Dehydroxylated 19-Nor-1(or 3),25-dihydroxyvitamin D3
R1
o-chloranil (3 eq.)
MeOH (2 eq.)
R2
OMe
O
CH2Cl2, rt
N
H
Functionalized Pyrrolinone
Li
O
H
O
K
OH
- +
O M
NR2
[2,3] Wittig
O - M'+
"Superbase"
OH
! Selective
OH
KH
LiNR2
!'
Koichi Mikami,* Kumiko Fujita, Kazuki Wakabayashi,
and Shigekazu Ito
O
!
CO2Bu-tert
up to 94 %, 100: 0
M=M'= Li or K
Li-K exchange
O-
- +
O K
OH
OH
-
!'
O
H
O
!' Selective
[2,3] Wittig Rearrangement
1171
High Regiocontrol in !-Deprotonation
Schlosser’s Mixed-Metal Amide Base
Kinetic Resolution of the Racemic 1-(Aryloxazol-2-yl)carbinols with Achiral Carboxylic Acids by Asymmetric
Esterification: A New Method for the Preparation of
Chiral 1,2-Amino Alcohols
Oxy-Cope Rearrangement
Vitamin D3
OH
H2N
Kenya Nakata, Keisuke Ono, and Isamu Shiina*
N
OH
kinetic resolution
O
R
dearomatization
(CH2)2Ph
85% ee
OH
H2N
(CH2)2Ph
>99% ee
Asymmetric Esterification
1181
Kinetic Resolution
1-(Aryloxazol-2-yl)carbinol
Asymmetric Synthesis of #-Siloxyenamides via Chiral
Auxiliary-Mediated Diastereoselective Coupling of
Ynamides, Aldehydes, and Silane by Nickel Catalyst
Chiral 1,2-Amino Alcohol
O
Nozomi Saito, Tomoyuki Katayama, and Yoshihiro Sato*
R1
O
N
O
+
H
BTM
O
cat. Ni(0)-SIMes
O
Et3SiH
R3
N
R2
OSiEt3
H
N
R2
N
* R3
R1
up to 99% de
SIMes
Ynamide
1189
Aldehyde
Nickel
Diastereoselective Coupling
Enamide
Hydrogen-Activated Benzylidynetricobalt Nonacarbonyl:
Carbonylative Cyclization of Enynes in Synthesis Gas
without Reducing Substrates and Products
Takumichi Sugihara,* Akihito Wakabayashi, Mugio Nishizawa,
and Shinobu Honzawa
Ph
MeO2C
MeO2C
+ CO gas
C
OC
CO
OC Co
Co CO
OC Co CO
OC
CO
CO
catalyst
Carbonylative Cyclization
Benzylidynetricobalt Nonacarbonyl
Hydrogen
Carbon Monoxide
Cyclopentenone
without H2
MeO2C
MeO2C
with H2
MeO2C
MeO2C
O
■ PAPERS
1195
Nucleophilic Reactions of 9-Isopropyl-2,4-dimethoxy7,12-dimethyl-3-(phenylsulfonyl)benzo[a]heptalene
with Lithium Dialkylamides
LDA, THF
–5 °C
Samir El Rayes, Anthony Linden, Khaled Abou-Hadeed,
and Hans-Jürgen Hansen*
+
66%
OMe
Benzo[a]heptalene
1203
Nucleophilic Dibenzothiophene Dioxide
N
SO2Ph
MeO
Aromatic Substitution
S
O
LDA as Nucleophile
O
MeO
1.3 : 1
O
S
O
Deprotonation of Diphenyl Sulfone
Autocatalysis and Organocatalysis with Kemp’s
Triacid Compounds
Dariush Ajami, Seiji Kamioka, Aaron C. Sather,
Richard J. Hooley, and Julius Rebek, Jr.*
Autocatalysis
1217
Organocatalysis
Self-Replication
Template Synthesis
2-Amino-3-(5-phenylfuran-2-yl)propionic Acids and
5-Phenylfuran-2-ylacrylic Acids are Novel Substrates
of Phenylalanine Ammonia-Lyase
Het
PAL
CO2H
CO2H
Het
pH 10.2
Csaba Paizs, Monica Ioana To"a, László Csaba Bencze,
Jürgen Brem, Florin Dan Irimie, and János Rétey*
Het
PAL
CO2H
Biocatalysis
1229
MIO Enzyme
Enantioselectivity
Enzyme Mechanism
Br
R1
R2
R1
N
R1
1239
Titanium
S Ligand
Banlai Ouyang, Jianjun Yuan, Qin Yang, Qiuping Ding,
Yiyuan Peng,* and Jie Wu*
X
N
N
R2
X
N
Ti
N
Se Ligand
Generation of 3-(1H-Isochromen-1-yl)-1H-indole
via Silver Triflate-Catalyzed Tandem Reaction of
2-Alkynylbenzaldehyde with Indole
CO2H
Het
NH2
Et
R2
R1
Porphyrin
+
H
4-Br
4-Cl
2-Cl
Br
Et
R2
Phthalocyanine
a
b
c
d
Chemical Synthesis
Preparation and Electrochemical Properties of
Phthalocyaninato Titanium(IV) and Porphyrinato
Titanium(IV) Benzenedichalcogenolates
Takeshi Kimura,* Kaori Amano, Arata Yamamoto,
and Toshiharu Namauo
R
Het
O
CO2H
Het
pH 8.8
NH2
R
NH2
R1
R2
N
N
R2
N
+
R2
R3
X = S or Se
R1 = OBu-n; R2 = H
R1 = Bu-tert and H; R2 = H
R2
R1
R1 = SMe; R2 = Et
R1
CHO
R1
R1
R2
HN
AgOTf
(10 mol %)
N
H
R3
DMF, rt
R1
O
R2
2-Alkynylbenzaldehyde
Indole
3-(1H-Isochromen-1-yl)-1H-indole
Silver Triflate
1251
R2
A New Synthetic Approach to Some Functionalized
Cycl[3.2.2]azine Derivatives
Hideyuki Muranaka, Akikazu Kakehi,* Hiroyuki Suga,
and Kennosuke Itoh
O
N
DDQ
SR1
1267
4(1H)-8,8a-Dihydro-1,4-thiazino[3,4,5-cd]indolizinone
Desulfurization
C (R3 = Ac)
X-Ray Analysis
N-Methyl-N-phenyl-5-oxa-1-azaspiro[2.5]oct-1-en-2-amine
— Synthesis and Reactions of a Synthon for an Unknown
$-Amino Acid
Ph
Michael Löpfe, Anthony Linden, and Heinz Heimgartner*
N
O
3-Aminotetrahydropyran-3-carboxylic Acid
1283
B (R3 = H)
Ac2O
Dehydrogenation
SR1
EtO2C
A
Cycl[3.2.2]azine
OR3
N
in collidine
S
EtO2C
R2
2H-Azirin-3-amine
Me
N
Z-Phe-OH
MeCN, 0 °C to rt
5-Oxa-1-azaspiro[2.5]oct-1-en-2-amine
2-[1,3-Bis(ethoxycarbonyl)azulen-6-yl]ethynyltriphenylphosphonium Bromide
EtO2C
XH
Me
O
X-Ray Crystallography
EtO2C
CO2Et
CO2Et
- Ph3PMeBr
in CHCl3
N
N
H
PPh3Br
PPh3Br
10a in DMSO
EtO2C
X
XH
12
11
CO2Et
EtO2C
CO2Et
BrPh3P+
HN
Ph
N
N
H
Ph
EtO2C
a: X=NH
c: X=O
3
H
N
Peptide Synthesis
NH2
CO2Et
10
Noboru Morita,* Shiro Moriyama, Kozo Toyota,
Masataka Watanabe, Shigeru Kikuchi, Shunji Ito,
and Kunihide Fujimori
Z
O
O
NH2
Me
17
Azulene
1297
2-Azulen-6-ylethynyltriphenylphosphonium Bromide
Synthesis of Highly Substituted Nitropyrrolidines,
Nitropyrrolizines and Nitropyrroles via MulticomponentMultistep Sequences within a Flow Reactor
2-Azulen-6-ylbenzoazole
O2N
Marcus Baumann, Ian R. Baxendale, Andreas Kirschning,
Steven V. Ley,* and Jens Wegner
6-(1H-Perimidin-2-yl)azulene
R1
R1
X
O
R2
Nucleophilic Addition
H
+ NEt3
R2
N
H
CO2Me
X = NO2, H
HCl. H2N
Flow Chemistry
1317
Micro-Reactor
Cycloaddition
Pyrrolidine
Heterocycle
Synthesis and Properties of N 1-(3-Methoxypropyl)N 3-methylimidazolium Salts
Eigo Miyazaki,* Nozomi Ishine, Kazuo Takimiya,* and
Hiroyuki Kai
Ionic Liquid
Imidazolium Salt
Low Viscosity
CO2Me
Dye-Sensitized Solar Cell
1327
Efficient Phenolic Oxidations to Construct orthoSpirolactone Structures Using Oxo-Bridged
Hypervalent Iodine(III) Compound
Ph
O
OH
Naoko Takenaga, Teruyoshi Uchiyama, Daishi Kato,
Hiromichi Fujioka, Toshifumi Dohi, and Yasuyuki Kita*
OCOCF3
I
Ph
O
O
I
O
OCOCF3
CO2H
R
R
11 examples
up to 99% yield
Ortho-Spirolactone
1337
Phenolic Oxidation
Hypervalent Iodine
µ-Oxo-Bridged Structure
A Molecular Orbital Calculation Study on the Interesting
Reactivity of Fluorine-Containing 3,4-Dihydro-2H-pyrans
with Aromatic Compounds in the Presence of
Trifluoroacetic Acid
Ar
Z = H, R = Et
OR
Norio Ota, Yasuhiro Kamitori,* Eisuke Nishiguchi, Makoto Ishii,
and Etsuji Okada*
EtO
O
rt
ArH
CF3CO2H
Z
EtO
CF3
O
CF3
Ar
Z = H, COCF3
R = Et, iso-Bu
COCF3
ref.
COCF3
Z = COCF3, R = iso-Bu
Fluorine-Containing Heterocycle
1345
Dihydropyran
Pyrylium
Molecular Orbital Calculation
Design and Synthesis of Telomestatin Derivatives
Containing Methyl Oxazole and Their G-Quadruplex
Stabilizing Activities
O
O
Satoki Majima, Masayuki Tera, Keisuke Iida, Kazuo Shin-ya,
and Kazuo Nagasawa*
N
H
N
Me
Me
N
O
N
N
O
Me
N
Me
NHAc
O
( )3
N
H
N
O
AcHN
O
( )3 O
L2A2-6M(4)OTD
G-Quadruplex
1359
Telomestatin
Oxazole
Methyl Oxazole
Structural Reevaluations of Amphidinol 3, a Potent
Antifungal Compound from Dinoflagellate
Nucleic Acid
OH
HO
2
OH
Respati T. Swasono, Mitsunori Kanemoto,
Nobuaki Matsumori, Tohru Oishi, and Michio Murata*
OH
OH
68
Me
OH
OH
OH
30
OH
OH
Me
OH 69
HO
HO
Amphidinol 3 (AM3)
67
60
C49
HO
H-51
HO
1371
Conformation
Hairpin Configuration
H-51
Toroidal Pore
Yusuke Mikami, Kaori Ebata, Takato Mitsudome,
Tomoo Mizugaki, Koichiro Jitsukawa, and
Kiyotomi Kaneda*
Catalyst
Organic Hydride
Hydrogenation
C52
HO
configurational change
Reversible Dehydrogenation-Hydrogenation of
Tetrahydroquinoline-Quinoline Using a Supported
Copper Nanoparticle Catalyst
Copper Nanoparticle
O
H
Dehydrogenation
H-50
OH
H
OH
confirmation by
acetylation
OH
O
H
OH
40
70
C49
C50
H-50
C52
H
C49
C50
OH
OH
50
HO
Marine Toxin
HO
20
10
AcO
H-51
C50
AcO
H-50
C52
OH
1379
R
A Cyclic Acetal Tethered Intramolecular Diels-Alder
Cycloaddition. Studies Directed toward a Total
Synthesis of (±)-Fusidilactone C
1
O
Sunil K. Ghosh, Yonggang Wei, Aleksey I. Gerasyuto,
John B. Feltenberger, Jiashi Wang,* and Richard P. Hsung*
HO
8a
HO
O
4
O
B
O
F
4a
11
A
3
O
2"
10
OP
C
OH
E
5
cyclic acetal tethered
R1
intramolecular
Me
O
Diels-Alder
O
cycloaddition
TS-endo-I – Boat-Boat
P1O
3
C
9
O
O
Et
O
B
1411
Endo-Selective Intramolecular Diels-Alder Cycloaddition
Enantioselective Synthesis of $-Methylene-#butyrolactams Using N-tert-Butanesulfinamides
Oxo-Adamantane Skeleton
Br
Haythem K. Dema, Francisco Foubelo,* and Miguel Yus*
S
N
+
R
TS-exo-II – Chair-Boat
O
HN
In, NaBr-H2O
Bu-tert
23 °C, 12 h
H
2
1
R
H-Bonding
O
EtO2C
R1
Me
O
desired for the
total synthesis
Usidilactone C
O
O
A
fusidilactone C
Cyclic Acetal
versus
O
O
3'
OP
EtO2C
S
Bu-tert
Ph
3 (72-82%, 86:14-95:5 dr)
[R = Me(CH2)7, iso-Pr, Ph(CH2)2, Ph]
1) HCl-dioxane, MeOH, 0 °C
2) NaOMe-MeOH, 0 °C
R
O
N
H
4 (90-95%, >95% ee)
!-Methylidene-#-butyrolactam
1423
Diastereoselective Allylation
N-tert-Butanesulfinimine
Indium
Preparation of "-Amino Esters and "-Lactams from
Nitriles via Aldimine-Borane Complexes
N
H
P. Veeraraghavan Ramachandran,* Debanjan Biswas,
and Guang-Ming Chen
R
R
N
ZnI2 (cat.)
Et2O, 0.5 h, rt
BEt3
NH2
CO2Me
OSiMe3 R
H
OMe
2 h, rt
MeMgBr
ref, 2d
O
HN
R
58-74%
Nitrile
1435
Aldimine
$-Amino Ester
$-Lactam
Cycloaddition
Transformations of Dimethyl (2E,3E)-2-[(Dimethylamino)methylene]-3-(1-methyl-2,5-dioxoimidazolidin-4-ylidene)succinate with C-Nucleophiles
Uro% Ur%i&, Jurij Svete, and Branko Stanovnik*
Me
R
N
O
O
NH
NMe2
MeO2C
N
O
R
O
O
N
O
MeO2C
O
O
CO2Me
O
CO2Me
O
NH
Me
N
Me
O
N
O
MeO2C
MeO2C
O
N
Me
O
N
N Me
O
3-(1-Methyl-2,5-dioxoimidazolidin-4-ylidene)succinate
1447
(1H-Imidazol-4-yl)but-2-enedioate
Synthesis of Macrobi- and Macrotricyclic Compounds
Comprising Pyrimidyl Substituted Cyclen and Cyclam
Sergei M. Kobelev, Alexei D. Averin, Alexei K. Buryak,
Franck Denat, Roger Guilard,* and Irina P. Beletskaya*
R
n
N
R
N
N
N
n
N
R = H,
n = 0, 1
Amination
Polyamine
Pd Catalysis
Pyrimidine
Br
H2N
X
NH2
n
N
N
N
N
Pd(dba)2/BINAP
N
Br
Macrocycle
1H-Pyrrolo[1,2-c]imidazole-6,7-dicarboxylate
n
tert-BuONa, dioxane, ref.
N
N
N
N
X
HN
NH
1477
Step-Growth Control in Template-Directed Polymerization
Xiaoyu Li, Andres F. Hernandez, Martha A. Grover,
Nicholas V. Hud, and David G. Lynn*
Self-Organization
1489
Chemical Evolution
Molecular Information Storage and Transfer
Synthesis of New Biheterocycles by a One-Pot
Sonogashira Coupling Reaction
Mandar Deodhar, David StC Black,* and Naresh Kumar*
Het-X
R1
1503
Biheterocycle
Synthetic Methodology
Het
2) DBU, Het-X
O
Het-X =
R2
Sonogashira Coupling Reaction
1) H
SiMe3
PdCl2(PPh3)2, CuI, TEA
Het
Br
OMe
I
I
O
N
H
MeO
OMe
Biflavone
MeO
Biindole
Me
Me
Jan-Erik Damke, Torben König, Gerold Haake,
Lechos'aw Latos-Gra(y)ski, and Franz-Peter Montforts*
Me
Me
Me
N
N
NC
CN
Me
N
O
R
Me
Me Ni
1515
Me
Me
R
2'
CN
8 R=H
14 R = Me
Oxotetrahydrobilin
N
O
HN
rac-14
Me
Me
N
N
Me
Me
OEt
CHO
1
NC
Me Ni
HN
Nickel Tetrahydrobilin
O
Me
Unusual Oxidation in the Course of Synthesis of
N-Confused Nickel Tetrahydrobilins
OMe
O
rac-20 R = H
rac-21 R = Me
Unusual Oxidation
$,$-Dichloroisoxazolidinones for the Synthesis
and Chemoselective Peptide Ligation of $-Peptide
$-Ketoacids
O
Ph
HN
CO2H
+
O
R1
Cl
Tetsuo Narumi and Jeffrey W. Bode*
!-amino acid
O monomer
Cl
1:1 oxalic buffer-MeOH
40 °C
R1
O
Ph
N
H
CO2H
Cl
potassium
oxalate (aq.)
80 °C
R1
O
Ph
CO2H
N
H
Cl
O
!-peptide-!-keto acid
Peptide
1527
Isoxazolidine
!-Keto Acid
Amide
Asymmetric Synthesis
Deconstructing Quinine. Part 1. Toward an Understanding
of the Remarkable Performance of Cinchona Alkaloids in
Asymmetric Phase Transfer Catalysis
Scott E. Denmark* and Robert C. Weintraub
Br
X
N
Y
N
Br
N
X
N
Ph
Phase Transfer Catalysis
Cinchona Alkaloid
Asymmetric Alkylation
CO2Bu-tert +
OH
Y
N
N
Y
Y
Ph
N
cinchonidine
Cinchona catalyst
(2.5 mol%)
50% KOH aq.
Br
toluene
2-4 °C
Structure/Activity/Selectivity Relationships
Ph
N * CO2Bu-tert
Ph
Ph
Chiral Ammonium Salt
1541
Convenient Synthesis of the Key Intermediate for
Dihydrocorynantheol and Protoemetinol from the
Monoacetate of 4-Cyclopentene-1,3-diol
O
HO
O
N
Yuichi Kobayashi,* Kaori Yagi, and Yuki Kaneko
H
OTBDPS
OAc
OH
dihydrocorynantheol
protoemetinol
Dihydrocorynantheol
1549
Protoemetinol
4-Cyclopentene-1,3-diol
Stereoselective Reaction
*-Lactone
NH2
Non Covalent Inclusion of Nucleosides and Nucleotides
in Water-Soluble Molecular Clips
N
R
Frank Bastkowski, Jolanta Polkowska, Thomas Schrader,*
and Frank-Gerrit Klärner*
N
R
OH
N
2
N
O
R
NH2
N
R
O
OH
OH
OH
O
O
N
1: R = OPO32- 2 Li+
2: R =
OP(Me)O2-
Host-Guest Complex
R
O
OH
OH
n-Pr
#E(5-6) = 6.95 kcalmol-1
#E(5-7) = 4.71 kcalmol-1
O
O
toluene
130 °C, 50 psi
(R)-(+)-!- or
(S)-(")-! or (+)-!-MBA
E
N
E
R
G
Y
O
HO
NaOH
n-Pr
THF-MeOH
ref.
5
n-Pr
n-Pr
O
O
O
HO
O
O
O
7
O
6
1577
Michael Addition
C-Alkylation
#E(6-7) = 2.24 kcalmol-1
O-Alkylation
De Novo Asymmetric Approach to the Disaccharide
Portion of SCH-47554
Me
O
O
O
HO
Xiaomei Yu, Miaosheng Li,* and George A. O'Doherty*
O
Me
O
O
OH
O
O
!-L-aculose
Me
O
OH
O
O
O
O
n-Pr
n-Pr
Phthalide
OH
Differentiated Cyclization of the Ketoacid Derived from
Tokinolide B
Alejandra León, Rubén A. Toscano, J. Antonio Cogordán,
and Guillermo Delgado*
O
N
O
Supramolecular Chemistry
O
1567
Nucleotide
NH
NH2
N
O
OH
Molecular Clip
NH
N
R
Li+
O
N
O
O
SCH-47554 (1)
OPiv
4
!-D-amicetose
"-L-aculose
De Novo Asymmetric Synthesis
1585
Noyori Reduction
Aculose
SCH7554
Amicetose
A Convenient Entry to New C-7-Modified Colchicinoids
through Azide Alkyne [3+2] Cycloaddition: Application
of Ring-Contractive Rearrangements
Norman Nicolaus, Jens Reball, Nikolay Sitnikov,
Janna Velder, Andreas Termath, Alexey Yu. Fedorov,
and Hans-Günther Schmalz*
1,2,3-Triazole
Click Chemistry
N3
NHAc
MeO
MeO
O
Alkaloid
Antitumor Compound
cat. Cu(I)
"CLICK"
MeO
MeO
OMe
1,3-Dipolar Cycloaddition
Rdiv
MeO
MeO
R
R = CO2Me, OH
Rearrangement
MeO
N
MeO
N N
Rdiv
MeO
R
1601
Design and Synthesis of Photocleavable BiotinylatedDopamine with Polyethyleneoxy Photocleavable Linkers
Kengo Hanaya, Yoshiyuki Kageyama, Masanori Kitamura,
and Shin Aoki*
h!
Linker
h!
photocleavable
QB unit
Avidin
Photo Reaction
1617
Quinolinol
Sulfonate
Biotin
QCM
Synthesis of 2- and 3-Indolylpyrroles via 1,3-Dipolar
Cycloadditions of Münchnones and Nitroalkenes
O
R1
O
R1
N
Justin M. Lopchuk and Gordon W. Gribble*
N
N,N'-diisopropylcarbodiimide
THF, ref.
R3
R3
H
R2
Bn
R1, R2 = Me, Ph
NO2
= H, Me, SO2Ph
N
Bn
R2
N
R3
24 examples
Mesoionic
1633
Cycloaddition
Regioselectivity
Regiospecific Rearrangement of Hydroxylamines to
Secondary Amines Using Diisobutylaluminum Hydride
Hidetsura Cho,* Kenji Sugimoto, Yusuke Iwama,
Nakako Mitsuhashi, Kentaro Okano, and
Hidetoshi Tokuyama*
X
X
DIBALH
n
n
N
H
NHOH
n = 1, 2, 3
n = 1, 2, 3
X = CH2, S, O
Diisobutylaluminum Hydride
Hydroxylamine
Reductive Ring Expansion Reaction
Rearrangement
Synthesis of a Chiral C3-Symmetric Bowl-Shaped
Cyclohexapeptide Composed of Anthranilic Acid
and Leucine
H
Motohiro Akazome,* Masashi Enzu, Yohei Goto,
and Shoji Matsumoto
O
N
O H
O
N
N
O
H
N
N
O
H
1
Peptide Synthesis
Aminobenzoic Acid
Chiral Bowl Shape
Hydrogen Bond
N H
H
O
Conformation
H
N
R
N
H
m = 0, 2
X = CH2, S, O
■ NOTES
1645
m
Partial Phenonium Cation
R = Me, Et, Ph
1657
The Preparation of Ketene Dithioacetals and Thiophenes
from Chloropyridines Containing an Active Methylene
Group
R1
Keith R. Sturrock,* David H. Bremner, and Grant Wishart
a
Cl
N
Cl
SCH2R2
SCH2
N
R2
R3
R1
S
b
R2
Cl
SCH2R2
N
R1, R2 = CN, CO2Et; R3 = NH2, OH
a: NaH, DMSO, CS2, ClCH2R1; b: NaOEt, EtOH
Base Catalysed Reaction
1663
Cyclization
Thorpe Reaction
Dieckmann Reaction
Synthesis of Polycyclic Aromatics from a Diiodosultine
by Suzuki-Miyaura Cross-Coupling and Diels-Alder
Reaction
I
Sambasivarao Kotha* and Milind Meshram
I
Carbon Disulfide
Ar
Br
1) Rongalite
Br
2) Suzuki!Miyaura
coupling
Ar
3) Diels!Alder reaction
Polycyclic Compound
1669
Building Block Approach
Diels-Alder Reaction
Suzuki-Miyaura Cross-Coupling Reaction
Boronic Acid
OR
Synthesis of C3 and Cs Symmetric Cyclic Triglycerols
Masahiro Hamada, Ryou Fujiwara, Takao Kishimoto, and
Noriyuki Nakajima*
O
OR
O
O
O
RO
OR
O
O
RO
C3-symmetric form
OR
Cs-symmetric form
R = Bn and H
Cyclic Polyglycerol
1675
Glycerin Oligomer
Authentic Standard
Crown Ether
An Efficient Synthesis of Antibiotic SF-2312
(3-Dihydroxyphosphoryl-1,5-dihydroxy-2-pyrrolidone)
O
Tadashi Hanaya* and Chika Itoh
Phase Transfer Catalyst
O
(EtO)2P
(HO)2P
1) OsO4, NaIO4
O
O
2) deprotection
NH
N
OH
OBn
SF-2312
Phosphonic Acid
1685
Hydroxamic Acid
Antibiotic
2-Pyrrolidone
C-P Bond
OH
New Oxidation Products from (-)-Epigallocatechin
Gallate in Neutral Solution
Takayo Ohyabu, Shoko Taniguchi, Hideyuki Ito, and
Tsutomu Hatano*
OH
HO
CO
O
O
HO
H
O
H
CO
Epigallocatechin Gallate
Catechin
Tannin
Oxidation
HO
OH
O
HO
H
H
H
H
OH
CO
CO2H
O
O
O
OH
HO
3
O
O
O
OH
CO2H
OH
OH
OH
OH OC
OH
OH
HO
Polyphenol
HO
O
O
OH
OH
OH
HO
OH
4
O
OH
OH
1693
Polymyrifline A, a New Polymethoxyflavone from
Citrus aurantium var. myrtifolia
OMe
8
MeO
Yusuke Hirasawa, Mari Hirata, Katsuya Haruna,
Masahiro Takeda, Kazunori Ogawa, and Hiroshi Morita*
5
1'
O
9
O
O
OMe O
Citrus aurantium var. myrtifolia
1699
Polymyrifline A
Polymethoxyflavone
Synthesis of 6-Deoxy-D-altrose Used as an Authentic
Sample to Identify an Unknown Monosaccharide
Isolated from the Fruiting Body of an Edible Mushroom
Masashi Yamada, Fumi Yoshida, Hiromune Ando,
Hideharu Ishida,* Makoto Kiso, and Masakuni Tako
OH
OH
O
HO
OH
HO
1705
Rare Sugar
D-Mannose
D-Rhamnoside
OR1
OH
Me
O
O
HO
R1O
OH
OR2
D-mannose
6-Deoxy-D-altrose
OH
OH
OH
1
Me
R1O
1''
6''
NO Production Inhibitory Activity
OMe
OH
3'
2
4
10
OMe
4'
OH
D-rhamnoside
6-deoxy-D-altrose
Mushroom
O
Second Generation Palladium-Catalyzed
Cycloalkenylation in Iridoid Lactone Synthesis:
Total Syntheses of (±)-Onikulactone and
(±)-Mitsugashiwalactone
O
H
O
H
O
Megumi Saeki and Masahiro Toyota*
Onikulactone
1709
Mitsugashiwalactone
Iridoid Lactone
H
onikulactone
mitsugashiwalactone
Cycloalkenylation
Lactone Ester
Synthesis of Selenohydantoins from Isoselenocyanates
and $-Amino Acids
Hajime Maeda,* Koichi Sakata, Masaru Takashima,
Tatsuya Watanabe, Nobuteru Mizukami, Mitsunori Honda,
and Masahito Segi*
Selenium
1719
H
Nucleophilicity
Cumulene
Condensation
R1 N C Se
+
Se
R2
R3NH
R1
CO2H
N
O
Heterocycle
H
Structures of Fukinone Epoxides. Configuration,
Conformation, and CD Spectra
H
O
O
O
O
Yoshinori Saito and Motoo Tori*
H
Me
H
Me
CD [!]: -2860 (300.4 nm)
CD Spectra
Epoxy Ketone
Absolute Configuration
Fukinone
X-Ray Analysis
Me
Me
O
O
Me
Me
Me
O
Me
+780 (309.7 nm)
O
N
R3
R2
1727
Asymmetric Intramolecular Aldol Reaction Mediated
by (S)-N-Substituted-N-(2-pyrrolidinylmethyl)amine to
Prepare Wieland-Miescher Ketone
Yuichi Akahane, Kohei Inomata,* and Yasuyuki Endo
O
H
N
N
H
O
R
O
TFA
O
O
Organocatalysis
1739
Wieland-Miescher Ketone
N-Substituted-N-(2-pyrrolidinylmethyl)pyrrolidine
Chiral Synthesis
Oxidative Coupling of Indoles with 3-Oxindoles
Mikkel Jessing and Phil S. Baran*
OH
N
H
1 eq.
Indole
Oxindole
■ INDEXES
1747
1767
Author Index
Subject Index
Oxidative Coupling
Alkaloid
Oxidation
CO2Me +
R
H
N
2 eq.
NaHCO3 (3 eq.)
MeCN (0.1 M), 0 oC;
CAN (2 eq.), rt
O
N
H
H
N
CO2Me
R
■ ADDITIONS AND CORRECTIONS
1775
Immobilisation of the Vitamin B12 Derivative B12-Tyramide
on Electrode Surfaces
Luisa M. Abrantes, Jorge P. Correia, Ana M. Tenreiro, and
Reinhart Keese*
Contributors
To This Issue
1137
Abe, Hajime
1669
Fujiwara, Ryou
1195
Abou-Hadeed, Khaled
1127
Fukuyama, Yoshiyasu
1203
Ajami, Dariush
1379
Gerasyuto, Aleksey I.
1727
Akahane, Yuichi
1029
Ghosh, Indranath
1645
Akazome, Motohiro
1379
Ghosh, Sunil K.
1229
Amano, Kaori
1645
Goto, Yohei
1699
Ando, Hiromune
1617
Gribble, Gordon W.
1601
Aoki, Shin
1477
Grover, Martha A.
1447
Averin, Alexei D.
1447
Guilard, Roger
1137
Azuchi, Junichi
1503
Haake, Gerold
1739
Baran, Phil S.
1669
Hamada, Masahiro
1549
Bastkowski, Frank
1601
Hanaya, Kengo
1297
Baumann, Marcus
1675
Hanaya, Tadashi
1297
Baxendale, Ian R.
1195
Hansen, Hans-Jürgen
1447
Beletskaya, Irina P.
1127
Harada, Kenichi
1217
Bencze, László Csaba
1693
Haruna, Katsuya
1423
Biswas, Debanjan
1083
Hashimoto, Yuichi
1489
Black, David StC
1685
Hatano, Tsutomu
1515
Bode, Jeffrey W.
1029
Hauck, Sheila I.
1217
Brem, Jürgen
1267
Heimgartner, Heinz
1657
Bremner, David H.
1477
Hernandez, Andres F.
1029
Brielmann, Harry L.
1127
Hioki, Hideaki
1693
Hirasawa, Yusuke
917 Buciumas, Ana-Maria
1447
Buryak, Alexei K.
1693
Hirata, Mari
1423
Chen, Guang-Ming
1709
Honda, Mitsunori
1137
Chiba, Junya
1189
Honzawa, Shinobu
1029
Chiu, Melanie
1203
Hooley, Richard J.
1633
Cho, Hidetsura
1379
Hsung, Richard P.
1143
Huang, Pochi
1477
Hud, Nicholas V.
1345
Iida, Keisuke
Damke, Jan-Erik
1119
Iimura, Nahoko
981 De Cola, Chiara
1157
Inomata, Katsuhiko
949 Ciufolini, Marco A.
1567
Cogordán, J. Antonio
949 Coqueron, Pierre-Yves
1503
1567
Delgado, Guillermo
1727
Inomata, Kohei
1411
Dema, Haythem K.
1137
Inouye, Masahiko
1447
Denat, Franck
1217
Irimie, Florin Dan
1527
Denmark, Scott E.
1119
Isaka, Nobuhisa
1489
Deodhar, Mandar
1699
Ishida, Hideharu
981 De Riccardis, Francesco
1119
Ishiguro, Masaji
1239
Ding, Qiuping
1337
Ishii, Makoto
1327
Dohi, Toshifumi
1083
Ishikawa, Minoru
1137
Doi, Yasuhiro
1317
Ishine, Nozomi
1371
Ebata, Kaori
1685
Ito, Hideyuki
1195
El Rayes, Samir
1163
Ito, Shigekazu
1727
Endo, Yasuyuki
1283
Ito, Shunji
1645
Enzu, Masashi
1675
Itoh, Chika
1127
Esumi, Tomoyuki
1251
Itoh, Kennosuke
1585
Fedorov, Alexey Yu.
1633
Iwama, Yusuke
1379
Feltenberger, John B.
1157
Iwamoto, Ryoji
1411
Foubelo, Francisco
1143
Iyoda, Masahiko
1283
Fujimori, Kunihide
1157
Fujinami, Shuhei
1029
Jacobi, Peter A.
1327
Fujioka, Hiromichi
1151
Jang, Young P.
1163
Fujita, Kumiko
1739
Jessing, Mikkel
981 Izzo, Irene
1371
Jitsukawa, Koichiro
1633
Mitsuhashi, Nakako
1585
Schmalz, Hans-Günther
1601
Kageyama, Yoshiyuki
1317
Miyazaki, Eigo
1549
Schrader, Thomas
1317
Kai, Hiroyuki
1371
Mizugaki, Tomoo
1709
Segi, Masahito
1251
Kakehi, Akikazu
1709
Mizukami, Nobuteru
1171
Shiina, Isamu
1203
Kamioka, Seiji
1503
Montforts, Franz-Peter
1133
Shindoh, Naoya
1337
Kamitori, Yasuhiro
1693
Morita, Hiroshi
1345
Shin-ya, Kazuo
1371
Kaneda, Kiyotomi
1283
Morita, Noboru
1137
Shirato, Wataru
1541
Kaneko, Yuki
1283
Moriyama, Shiro
1585
Sitnikov, Nikolay
1359
Kanemoto, Mitsunori
1083
Motoshima, Kazunori
1113
Sohn, Te-ik
1181
Katayama, Tomoyuki
1251
Muranaka, Hideyuki
1007
Somei, Masanori
1327
Kato, Daishi
1359
Murata, Michio
1435
Stanovnik, Branko
917 Kholod, Inga
1345
Nagasawa, Kazuo
1657
Sturrock, Keith R.
1283
Kikuchi, Shigeru
1669
Nakajima, Noriyuki
1251
Suga, Hiroyuki
1113
Kim, Byungsook
1151
Nakanishi, Koji
1189
Sugihara, Takumichi
1113
Kim, Deukjoon
1171
Nakata, Kenya
1633
Sugimoto, Kenji
1113
Kim, Sanghee
1229
Namauo, Toshiharu
1083
Sugita, Kazuyuki
1229
Kimura, Takeshi
1515
Narumi, Tetsuo
1435
Svete, Jurij
1297
Kirschning, Andreas
917 Neier, Reinhard
1359
Swasono, Respati T.
1669
Kishimoto, Takao
1585
Nicolaus, Norman
1119
Takada, Futa
1699
Kiso, Makoto
1337
Nishiguchi, Eisuke
1143
Takase, Masayoshi
1327
Kita, Yasuyuki
1143
Nishinaga, Tohru
1709
Takashima, Masaru
1601
Kitamura, Masanori
1143
Nishiuchi, Tomohiko
1133
Takasu, Kiyosei
1549
Klärner, Frank-Gerrit
1189
Nishizawa, Mugio
1693
Takeda, Masahiro
1541
Kobayashi, Yuichi
1083
Noguchi-Yachide, Tomomi
1133
Takemoto, Yoshiji
1447
Kobelev, Sergei M.
1577
O'Doherty, George A.
1327
Takenaga, Naoko
1503
König, Torben
1693
Ogawa, Kazunori
1317
Takimiya, Kazuo
1663
Kotha, Sambasivarao
1685
Ohyabu, Takayo
1699
Tako, Masakuni
1127
Kubo, Miwa
1359
Oishi, Tohru
1119
Tamiya, Minoru
1127
Kubo, Naoko
1337
Okada, Etsuji
1127
Tanabe, Kazuma
1489
Kumar, Naresh
1633
Okano, Kentaro
1685
Taniguchi, Shoko
1029
Lanz, Sandra
1029
O’Neal, William G.
1029
Tassa, Carlos
1503
Latos-Gra!y"ski, Lechos#aw
1171
Ono, Keisuke
1345
Tera, Masayuki
1113
Lee, Jongkook
1337
Ota, Norio
1585
Termath, Andreas
1567
León, Alejandra
1239
Ouyang, Banlai
1103
Tokitoh, Norihiro
1029
Leung, Sam
1217
Paizs, Csaba
1633
Tokuyama, Hidetoshi
1297
Ley, Steven V.
1239
Peng, Yiyuan
1719
Tori, Motoo
1577
Li, Miaosheng
1029
Pippin, Douglas
1217
To$a, Monica Ioana
1477
Li, Xiaoyu
1549
Polkowska, Jolanta
1567
Toscano, Rubén A.
1029
Li, Yongkai
1029
Pollina, Elizabeth
1283
Toyota, Kozo
1195, 1267 Linden, Anthony
1029
Pratt, Benjamin A.
1705
Toyota, Masahiro
1029
Liu, Hui
1423
Ramachandran, P. Veeraraghavan
1327
Uchiyama, Teruyoshi
1617
Lopchuk, Justin M.
1585
Reball, Jens
1157
Ukaji, Yutaka
1267
Löpfe, Michael
1203
Rebek, Jr., Julius
1435
Ur%i&, Uro%
1029
Löwer, Franzisca
1217
Rétey, János
1477
Lynn, David G.
1029
Robert, Frédéric
1585
Velder, Janna
1709
Maeda, Hajime
1029
Roberts, William P.
1189
Wakabayashi, Akihito
1345
Majima, Satoki
1705
Saeki, Megumi
1163
Wakabayashi, Kazuki
1359
Matsumori, Nobuaki
1181
Saito, Nozomi
1029
Wang, Hui
1645
Matsumoto, Shoji
1719
Saito, Yoshinori
1379
Wang, Jiashi
1663
Meshram, Milind
1709
Sakata, Koichi
1283
Watanabe, Masataka
1103
Mieda, Eiko
1157
Sakata, Ryo
1709
Watanabe, Tatsuya
1163
Mikami, Koichi
1103
Sasamori, Takahiro
1297
Wegner, Jens
1371
Mikami, Yusuke
1203
Sather, Aaron C.
1379
Wei, Yonggang
1371
Mitsudome, Takato
1181
Sato, Yoshihiro
1527
Weintraub, Robert C.
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1657
Wishart, Grant
1239
Wu, Jie
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Yagi, Kaori
1699
Yamada, Masashi
1229
Yamamoto, Arata
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Yanase, Emiko
1239
Yang, Qin
1699
Yoshida, Fumi
1577
Yu, Xiaomei
1239
Yuan, Jianjun
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Yus, Miguel
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