htr_main (jielde)

Transcription

htr_main (jielde)

HETEROCYCLES, Vol. 88, No. 2, 2014
■ REVIEWS
827
The Halogen/Magnesium-Exchange Using i PrMgCl!LiCl
and Related Exchange Reagents
Br
Br
N
Nadja M. Barl, Veronika Werner, Christoph Sämann, and
Paul Knochel*
N
Br
N
N
845
Grignard Reagent
Heterocycle
OP(O)(OEt)2 MeO
R23Al
cat. (!)-(NMI)2ZrCl2
R1
MKC - 442
(emivirine)
NH2
MeO
N
N
OtBu
N
O
N
OMe
81%
trimethoprim
R2
NH2
O
Me
O
6
OH
10
15
NH
O
(+)-scyphostatin
Pd or Cu-Catalyzed Cross-Coupling
fluvirucinine A1
Lipase-Catalyzed Acetylation
R
R
R
Martina Zatloukalová, Jan Vacek, and Vilím !imánek*
R
N
R
R
R
R
+
N
R
R
O
NH
8
Electrochemical Behaviour of Alkaloids: Detection
and Interaction with DNA and Proteins
Me
R
cyclic
voltammetry
R
Me
R
R
R
R
N
R
R
Electrochemical Detector
OH
O
HO
5
(!)-spongidepsin
ZACA Reaction (Zirconium-Catalyzed Asymmetric Carboalumination of Alkenes)
R2
OH
R1
70!95% ee
O2
AlR22
R1
ZACA
13
Voltammetry
N
MeO
OMe
O 1
Ph
Polarography
O
OtBu
MeO
Syntheses of Chiral Heterocyclic Compounds via
Zirconium-Catalyzed Asymmetric Carboalumination
of Alkynes (ZACA Reaction)
Alkaloid
Me
N
H
O
Magnesium
Shiqing Xu and Ei-ichi Negishi*
879
N
OMe
87%
OMe
DME, 60 °C, 1 h
Exchange Reaction
Me
N
MeO
2) MeO
OtBu
Ph
OEt
OMe
N
1) iPrMgCl·LiCl
THF, 0 °C, 4 h
OtBu
Br
2) LaCl3·2LiCl
Me2CO
0 °C, 4 h
OMe
OH
Me
Me
1) iPrMgCl·LiCl
25 °C, 15 min
OMe
Me
O
Interaction with Biopolymer
■ COMMUNICATIONS
899
Synthesis of the ABCD Ring System of Vinca Alkaloids
Using Tandem Intramolecular [2+2]PhotocycloadditionRetro-Mannich Fragmentation
James D. White* and Yang Li
HN
EtO2C
N
Boc
Indole
Tetracycle
Photocycloaddition Reaction
Vindoline
Vindorosine
N
O
N
Boc
N
O
CO2Et
N
Boc
R
H
O
CO2Et
911
Synthesis of p-tert-Butylcalix[4]thiacrowns Exhibiting
Sulfur Number-Dependent Complexation with
Mercury(II) Ion
But But
But
But
Tatsuya Takimoto,* Hirohito Tsue, Hiroki Takahashi,
Rui Tamura, and Hideaki Sasaki
O HOOHO
S
Calix[4]thiacrown
919
Synthesis
Complexation
S
OH
Ph
O
+
N
DCE, 60
Organocatalyst
O
O
P
O
OH
or
SH
MeO
R1
Nozomi Saito,* Ken-ichi Nakamura, and Yoshihiro Sato*
N
R N N N
R1
N
R N N N
R1
N
N
R
[1,2,3]triazolo[4,5-b]pyridines
N
[1,2,3]Triazolo[4,5-b]pyridine
[1,2,3]Triazolo[4,5-c]pyridine
O
John Boukouvalas* and Vincent Albert
O
MeO
O
3 steps
OH
O
73% overall
945
Natural Product
Total Synthesis
Maleic Anhydride
Chiral Memory Units Based on Dynamic Redox Systems
with a Dibenzoxepinone Skeleton: Drastic Change in
Racemization Barrier and Electrochemical Bistability
X
Kazuhisa Wada, Yuna Chiba, Takashi Takeda,
Hidetoshi Kawai, Ryo Katoono, Kenshu Fujiwara,
and Takanori Suzuki*
X
O
(P)-1a,b
(M)-1a,b
Carbocation
Redox System
X
X
2e-
2eO
easy
Chiral Memory
antrodin A
O
commercially available
Butenolide
N
N
R
N
Biomimetic Synthesis of Antrodia Maleimides and
Maleic Anhydrides
Maleimide
N
[1,2,3]triazolo[4,5-c]pyridines
N
2,3-pyridyne
939
R
N
N and/or
N
R1
N
R1
Azide
+ 2-mercaptopyridine: 78%
+ 8c: 70% (91% ee)
(20 mol%)
3,4-pyridyne
1,3-Dipolar Cycloaddition Reaction
O HO
Ph
Asymmetric Catalyst
1,3-Dipolar Cycloaddition of Pyridynes and Azides:
Concise Synthesis of Triazolopyridines
Pyridyne
4•Hg2+
O
HO
oC
MeO
(10 mol%)
Iron Catalyst
OH
Fe3O(CF3CO2)6(H2O)3
(3.3 mol%)
additive
O
additive
929
3•Hg2+
Hg2+
4 (n = 2)
n
O
Yohei Shimizu,* Kouji Yasuda, and Motomu Kanai*
Catalytic Reaction
3 (n = 1)
Mercury(II) Ion
A Catalytic C-C Bond-Formation with Minimal Use of
Protecting Groups: Construction of Functionalized
Isotetronic Acid Derivatives
Isotetronic Acid
Hg2+
Electrochromism
Helicity
electrochemical
bistability
O
O
(P)-2a,b2+
prohibited
(M)-2a,b2+
953
A Simple Route to Functionalized "1-Pyrrolines
Matilda Bingham, Cécile Moutrille, and Samir Z. Zard*
Cu(OAc)2
or
R" FeCl3
R'
AcO
N
R'"
R
Pyrroline
961
Oxime Ester
Intramolecular Substitution Reaction
No Catalyst, Radical Initiator and Photochemical
Irradiation Approach to Direct #-Trifluoromethylation
of Lithium Enolates
Yuichi Tomita, Toshiaki Iida, Ryota Hashimoto,
Yoshimitsu Itoh, and Koichi Mikami*
Direct "-Trifluoromethylation
969
Cu(II) Acetate
Lithium Enolate
Single Electron Transfer
H
A
O
975
O
B
C
O
Intramolecular Allylation
Development of Method for the Efficient #-Oxidation
of tert-Alkylamines Using bis(2,2,2-Trichloroethyl)
Azodicarboxylate
O
R N
CCl3CH2O
Amine
R'"
R
O
PG
H
H
O
E
D
N
CF3
R
OH
O
H H
H
OTBDPS
Ring-Closing Metathesis
gem-Diamino Compound
N
N
O
(1.2 eq.)
benzene, reflux, 3 h
R = MeCO- or Me3COCO"-Oxidation
R"
N
OCH2CCl3
Shinobu Honzawa,* Mitsuaki Uchida, and Takumichi Sugihara*
Azodicarboxylate Ester
or
R'
No Photochemical Irradiation
H
H
H
H
NAPO
Convergent Synthesis
R'
CF3I
No Radical Initiator
Kengo Shiroma, Hiroki Asakura, Tokihiro Tanaka,
Hiroyoshi Takamura, and Isao Kadota*
Ciguatoxin CTX3C
Cl
no catalyst
no initiator
no irradiation
Improved Synthesis of the A-E Ring Segment of
Ciguatoxin CTX3C
Marine Polycyclic Ether
R'"
Fe(III) Chloride
R
N
N
R
OLi
PG
R"
R N
O
CCl3CH2O
OCH2CCl3
N
N
H
O
■ PAPERS
981
Asymmetric Synthesis of Tertiary 2-Substituted
5-Oxotetrahydrofuran-2-carboxylic Acids
Anne Paju, Karolin Oja, Katharina Matkevit#, Priit Lumi,
Ivar Järving, Tõnis Pehk, and Margus Lopp*
O
substrate /Ti(OiPr)4/(+)-DET
1
0.2
0.32
OH
O
tBuO2H (2.5 eq); 48 h
R1
R2
Asymmetric Oxidation
997
Asymmetric Catalysis
R2
Spirolactone and Spirolactam
a R2= H; R1= -Bn;
b R2= H; R1= -Me;
c R2= H; R1= -C2H5;
O
d R2= H; R1= -CH2CH2OH;
CO2H e R2= H; R1= -CH CH OBn;
2
2
R1
f R2= H; R1= -CH2CH2NHBoc;
h R2= H; R1= -CH2CO2tAm;
i R2= -OSiMe2tBu; R1= -Bn;
2-2-Disubstituted 5-Oxotetrahydrofuran-2-carboxylic Acid
Synthesis of 2-Substituted 1,3-Cycloheptanedione
via a Lewis Acid Mediated Ring Expansion Reaction
R1
Kohei Inomata* and Yasuyuki Endo*
R1
HO
O
O
ZnI2
O
H
R1 = alkyl, branched alkyl, and Bn
2-Substituted 1,3-Cycloheptanedione
1013
Wieland-Miescher Ketone
Ring Expansion Reaction
Synthesis and Antimicrobial Evaluation of Oxazole-2(3H)thione and 2-Alkylsulfanyl-1,3-oxazole Derivatives
[2+2] Cycloaddition Reaction
S
O
O
I
1029
1,3-Oxazole
Thiocyanic Acid
Antibacterial Activity
S
Vasella's
fragmentation
S
O
O
R
HN
O
HO
OTBDMS
Antifungal Activity
A Deoxypodophyllotoxin-Based Sensor for Highly
Selective Recognition of Hg2+ Ion
O
Juanjuan Wang, Yuanyuan Yan, and Hui Xu*
O
O
O
O
O
O
O
Hg2+
N
OMe
N
HN
N
-HgS
Deoxypodophyllotoxin
Fluorescence Probe
Desulfurization Reaction
OMe
N
O
HN
S
1039
HN
dehydration
NH
TBDMSO
1,3-Oxazoline-2-thione
HSCN
OH
R
Sandrina Silva,* Filipa V. M. Silva, Jorge Justino,
Amélia Pilar Rauter, Patrick Rollin, and Arnaud Tatibouët
Lewis Acid
O
O
Natural Product
Mercury
Lewis Acid Catalyzed Diastereoselective 1,3-Dipolar
Cycloaddition between Diazoacetoacetate Enones and
Azomethine Ylides
Phong M. Truong, Michael D. Mandler, Charles S. Shanahan,
and Michael P. Doyle*
Ph
R2 =
Rh(II)
O
R1
O
O
R2
OMe
N2
diazoacetoacetate enone
(DAAE)
N
R2
OMe
AgOAc
R1
N2
MeO2C
Dipolar Cycloaddition Reaction
Silver Catalysis
Diazoacetoacetate Enone
H
H
O
Ph
CO2Me
R
N
Rh(II)
R2 = Ph
Pyrrolidine
R1
R
N
OMe
RN
MeO2C
O
O
MeO2C
Rh(II) Acetate
R1
O
CO2Me
1051
Zinc-Acetic Acid Promoted Reductive Carbon-Nitrogen
Bond Cleavage Reaction of #-Aminoketones
R3
O
N
Ar
Kyoko Ishikawa, Miyuki Tomatsu, Hiroshi Nagase,
and Hideaki Fujii*
O
Zn
R4
AcOH, rt
R1 R2
R3
H
Ar
+
H N
R4
R1 R2
O
Me
MeO
NH
AcOH, reflux
MeO
"-Aminoketone
1065
Selective Reductive C-N Bond Cleavage
Zinc-Acetic Acid Promoted Reaction
R
Jin-Peng Zhang, Wei Fan, Jie Ding, Bo Jiang,* Shu-Jiang Tu,*
and Guigen Li
H
+
OH H2N
+
O
MeO
O
N
NH
O
120 oC
O
N
N
1079
Pyrazole-Fused Benzo[h ]acridine
Photochemical Reactions of Prop-2-enyl and Prop-2-ynyl
Substituted 4-Aminomethyl- and 4-Oxymethyl-2(5H)furanones
O
Y
DMF
120 oC
R
Diego A. Fort, Thomas J. Woltering, André M. Alker, and
Thorsten Bach*
[2+2] Photocycloaddition Reaction
1101
Photochemistry
Cyclobutane
O
R
R = H, TMS
X = NBoc, O
O
X
Lactone
OH
The Paecilin Puzzle $ Enantioselective Synthesis of
the Proposed Structures of Paecilin A and B
Lutz F. Tietze,* Ling Ma, Stefan Jackenkroll,
Johannes R. Reiner, Judith Hierold,
Boopathy Gnanaprakasam, and Sven Heidemann
Y = H, Me, F
X = NBoc, NCbz
O, C(CO2Et)2
O
X
3 examples
53-92%
Spiro-Compound
O
R
h! ("= 254 nm)
rt (Et2O)
O
X
Y
14 examples
53-92%
O
R
Oxazole-Fused Pyrazolo[3,4-j ]acridine
h! ("= 254 nm)
rt (MeCN v Et2O)
O
X
NH4OAc
O
N
Microwave Irradiation
R'
H
N
NH
R
N
NH
R
O
HOAc
R'
Multicomponent Regioselective Domino Reaction
N
Activation of Carbonyl Group
O
Regioselective Multicomponent Domino Reactions
Providing Rapid and Efficient Routes to Fused Acridines
MeO
Zn
O
O
O CO2Me
O
O
MeO2C O
O
O
Enantioselective Reaction
1121
Paecilin
Palladium
Transition Metal Catalysis
OH
Wacker Oxidation
Rotational Energy Barrier around the C1–C11 Single Bond
in Lamellarins: A Study by Variable-Temperature NMR
Tsutomu Fukuda, Ryosuke Itoyama, Terufusa Minagawa,
and Masatomo Iwao*
MeO
R O
R
MeO
i-PrO
O
11
1
O
N
6
5
Rotational Energy Barrier
O
Oi-Pr
O
(aR)-isomer
Lamellarin Analogue
R
R
Variable Temperature NMR Measurement
rotation around
C1–C11 single bond
5,6-saturated: !G‡ 72–74 kJ/mol
5,6-unsaturated: !G‡ 83–87 kJ/mol
O
MeO
Oi-Pr
11
MeO
i-PrO
1
O
N
6
5
(aS)-isomer
O
1135
Formation of Unexpected Heterocyclic Products from
Pyrolysis of Thiocarbonyl Stabilised Phosphonium Ylides
H
Ph3P
O
S
R. Alan Aitken,* Graeme Barker, Lee P. Cleghorn,
Euan J. Reid, and Sheryl S. Roberts
R
Me H
P
OMe
1149
Pyrroloisoindole
1,4-Benzoxaphosphininium Salt
P
Me
X
O
But
(residue in inlet)
Pyrolysis
O
OMe
NHBoc
Aminophenylpyrrole
Pyrrolo[1,2-c]quinazolinone
Methyl Anthranilate
NHBoc
3-4 steps
Vinyl Grignard Reagent
HN
O
S
I
N
O
S
SS
Mg
H
MeO
RS
O
S
tert-Butanesulfinyl Imine
Total Synthesis of the Proposed Structures of
Eushearilide
Br
MeO
O
H
OMe
t-Bu
H
N
Me
(-)-cuspareine
OMe
OMe
OMe
Diastereoselective Addition
Wittig reaction
O
Takayasu Yamauchi,* Jun-ichi Takidaira, Kenya Okamoto,
Takaya Sugiura, Hiroki Horikoshi, Shintaro Kudo,
Shigeru Sasaki, Noriko Mizushima, and Kimio Higashiyama
3
16
Br
Me
t-Bu
Br
(-)-Cuspareine
N
Me
Me
(-)-angustureine
Br
t-Bu
HN
(-)-Angustureine
H
Br
Br
OH
Tetrahydroquinoline Alkaloid
O
O
H
t-Bu
Me
O
S
N
H
Copper-Catalyzed Cascade Reaction
Enantioselective Synthesis of Tetrahydroquinoline
Alkaloids (-)-Angustureine and (-)-Cuspareine from
Chiral tert-Butanesulfinyl Imines
H2N
R1
N
R1 or
N
R2
9 examples
Juan A. Sirvent, Francisco Foubelo,* and Miguel Yus*
1175
Ph
Aminophenylpyrrole Synthesis and Application to
Pyrrolo[1,2-c]quinazolinone Synthesis
Aurélie A. Dörr and William D. Lubell*
1163
O
But FVP, 550 °C
S
N
R
! Ph3PO
O
Ph
Phosphonium Ylide
FVP, 650 °C
N
H
S
20
23
O
O
P
NMe3
phosphate esterification
O
O
O
Shiina macrolactonization
Wittig reaction
(23S)- and (23R)-eushearilide
Macrolide
1191
Antifungal Activity
Shiina Reagent
Choline
Cycloaddition Reactions of Azide, Furan, and Pyrrole
Units with Benzynes Generated by the HexadehydroDiels–Alder (HDDA) Reaction
Junhua Chen, Beeraiah Baire, and Thomas R. Hoye*
hexadehydro-Diels–Alder cascades to polycyclic heterocycles
Me
O
Me
Aryne
Polycyclic Compound
Triazole
O
O
140 °C
H
OAc
12 h
O Me
O
Me
OAc
H
O
1201
Polyfluoroalkylation of Carbonyl Compounds
by Polyfluoroalkyl Anions Generated from
Polyfluorcarboxamides
O
Natshumi Wakita and Shoji Hara*
N
(Polyfluoroalkanoyl)piperidine
1213
Palladium Catalysis
Polyamine
O
O
Alexei N. Uglov, Georgii A. Zubrienko, Anton S. Abel,
Alexei D. Averin, Olga A. Maloshitskaya,
Alla Bessmertnykh-Lemeune, Franck Denat, and
Irina P. Beletskaya*
1233
CF3
2)
Macrobicycle
Ph
O
R
O
N
1.2 equiv
BF3-OEt2
1.1 equiv (Ss)-A
Ss t-Bu
O S
NH
N
R
Ph
Ph
!95% [!25:1]
Inversion of S-Center
O
1.1 equiv (Rs)-A
–78 oC to rt, 24 h
O
1255
HN
NH
X
A=
O S
H
Rs t-Bu
HOAc in
O S
NH H2O/THF
S
!
85 oC
Ph
O
1.2 equiv BF3-OEt2
H
O
Ellman-Davis Chiral Imine
N
Amination
Xiao-Na Wang, Richard P. Hsung,* Sierra K. Fox,
Ming-Can Lv, and Rui Qi
Lithiation
O
N
Pd(dba)2/L
tBuONa
dioxane
Br
Br
NH2
H2N
N
O
O
X
O
N
Synthesis of de novo Chiral %-Amino-ynamides Using
Lithiated Ynamides. Observation of a Unique 5-endo-dig
Cyclization with an Inversion of S-Center
Ynamide
R1
R2
F3C
R1R2C=O
Polyfluoroalkylation Reaction
Synthesis of Macrobicycles Comprising
2,7-Diaminonaphthalene Moiety via
Palladium-Catalyzed Amination Reaction
Macrocycle
OH
1) KBEt3H / THF
t-Bu
N
O
O
N
O
Ss
S NH
Ph
Ph
Ph
!95% [20:1]
33%: inversion at
S-center
N
and
Ph
O
HOAc in H2O/THF
O
N
85 oC
O R
s
S NH
O
O
and
Ph
Ph
N
S N
Ph
Ph
31%: inversion at S-center
20%-25%
5-endo-dig Cyclization
Chemoenzymatic Approach to Synthesis of
Hydroxylated Pyrrolidines from Benzoic Acid
David R. Adams, Johannes van Kempen, Jason R. Hudlicky,
and Tomas Hudlicky*
CO2H
CO2H
OH
R. eutrophus B9
OH
Cl
13 steps
OH
H2N
OH
OH
HO
Chemoenzymatic Synthesis
1275
Pyrrolidine
Azasugar
Iminosugar
Regioselective Bromination: An Approach to the
D-Ring of the Gilvocarcins
Ehesan U. Sharif and George A. O'Doherty*
O
X
O
A
B
OH
OMe
C
R
D
X = H, fucose
Regioselective Bromination
1,2,3,5-Tetrasubstituted Benzoic Acid
O
OMe
R = Me, Et, vinyl, alkynyl
Gilvocarcin
X
Boration
Br
MeO
M
OP O
X = H, fucose
Stannation
OP1
CO2Me
M = SnBu3, B(OR)2
P1 = alkyl or silyl group
HO
OH
CO2H
1287
Synthesis of Macrocyclic Dimer of Cyclic Hexaoxazole
and Examination of Its Interaction with Telomeric
Oligonucleotide
Keisuke Iida, Gen Tsubouchi, Takahiro Nakamura, and
Kazuo Nagasawa*
telomeric
G-quadruplex
macrocyclic-L2H2-6OTD-dimer
Telomestatin
1299
Telomeric G-Quadruplex
G-Quadruplex Ligand
Polyoxazole
Macrocycle
Synthesis of Functionalized 1-Azabicyclo[3.1.0]hexanes:
Studies towards Ficellomycin and Its Analogs
TBDPSO
Gang Chen, Zhi He, and Andrei K. Yudin*
H
CO2Me
NH
TBDPSO
N
CO2Me
N3
ficellomycin core
OH
OTBDPS
HN
PMBO
OPMB
H
N
OPMB
CH2OPMB
N3
ficellomycin core
Ficellomycin
1311
Aziridine
Cycloamination Reaction
Stereoselectivity
Regioselectivity
Total Synthesis of 8-epi-Javaberine A and Javaberine A
Yasutomo Yamamoto,* Yuri Tabuchi, Ayana Baba,
Kumiko Hideshima, Mai Nakano, Akari Miyawaki, and
Kiyoshi Tomioka*
OMe
OH
OMe
MeO
1)
NH
MeO
OH
OH
HO
HO2C
amidation
OH
HO
N
HO
H
2) Bischler-Napieralski
3) LiAlH4
OMe 4) BBr3
H
+
OH
OH
epi-javaberine A
Alkaloid Synthesis
Selective Formation of trans/threo/cis and cis/threo/cis
Bis-Tetrahydrofurans from the Same Diene Diols
Hiromichi Fujioka,* Tomohiro Oki, Tatsuya Hayashi,
Maki Yamakawa, Takeshi Kurachi, Kenji Nakahara,
Ryota Maehata, Tomohito Hamada, Kenichi Murai,
and Yasuyuki Kita
O
( )2
( )2
HO
OH
MeOH
O
I
1,2-Diamine
O
MeCN
(R3 = 2,4,6-triMeOC6H2)
O
cis/threo/cis
79% yield
MeO
OMe
R
Bz
N
NH
O
FeCl(dipic)(H2O)2
i-Pr2NH•HCl
H2O2 urea
2-Imidazolidinone
H2O2-Urea
R
HN
HO
MeC(OMe)3 (30%) Bz
in CH2Cl2
I
I(coll)2PF6
( )2
N
OMe
N SO Ar
2
O
DMIm
optical resolution
NH
MeO
O
racemic
OMe
S
S
HN
O OMe
(MAC-Cl)
Fe(III)-Catalyzed Oxidation
O
trans/threo/cis
75% yield
Cl
2-Imidazolone
O
Double Intramolecular Iodoetherification Reaction
Highly Efficient Preparation of Both Enantiomers of
Versatile Chiral Synthon for 1,2-Diamines via the
Fe(III)-Catalyzed Oxidation of 2-Imidazolone
Hirofumi Matsunaga,* Iori Eshita, Shoichi Tsunoda,
Naoko Ishimoto, Shin Ando, and Tadao Ishizuka*
I
(R1 = R2 = Me)
R1 R2
( )2
Selective Formation
MeOH
MeCN
O
R3
trans/threo/cis and cis/threo/cis-Bis-Tetrahydrofurans
I(coll)2PF6
( )2
( )2
O
1337
H
OH
javaberine A
1323
H
OH
OMe
8-Benzyltetrahydroprotoberberine
N
HO
N SO Ar
2
O
I
1355
Z
Z
Enantioselective Synthesis of Planar-Chiral Phosphines
with 1,N-Dioxa[N]paracyclophane Scaffold and Their
Application as Chiral Ligands
O
Kazumasa Kanda, Shoya Oshima, Tsubasa Shizuno,
Risa Hamanaka, Miku Fukai, and Takanori Shibata*
I
O
I
+
R
O
(CH2)n-2
Ph2P
O
O
1371
ortho-Lithiation
Chiral Ligand
up to 90% ee
O
Coupling Reaction
R
Synthetic Studies of Fisetin, Myricetin and Nobiletin
Analogs and Related Probe Molecules
OH
OH
Aiki Hiza, Yuta Tsukaguchi, Takahiro Ogawa, Makoto Inai,
Tomohiro Asakawa, Yoshitaka Hamashima, and
Toshiyuki Kan*
Me
R'
+ N
O
N
O
R'
N
R = H or OH
O
OH
R
R
O
OH
OH
O
HO
O
X=
O
HN
H
Me
O
NH
H O
S
O
fluorescent tag
Flavonoid
1397
Chemical Probe
Fluorescent Probe
R
PPh2
PPh2
Paracyclophane
O
O
chiral ligands
(CH2)n-2
Planar Chirality
R
cat. PdCl2(MeCN)2
cat. CuI
Biotin Probe
biotin tag
X
H
N
O
OH
O
Alzheimer's Disease
Synthesis and Reactions of 1,3,4-Selenadiazines
Wolf-Diethard Pfeiffer,* Harald Roßberg, Nazken Kelzhanova,
Amanzhan T. Saginayev, Alexander Villinger, and
Peter Langer*
R1
O
R2
Br
H2N
+
N
Se
R
R1
N
NHR3
R2
Se
N
R
NR3
R = H, Me
Cyclization Reaction
1433
Heterocycle
Selenium
Tautomerism
Formation of Xanthone Oxime and Related Compounds
Using a Combination of tert-Butyl Nitrite and Potassium
Hexamethyldisilazide
tert-butyl nitrite
KHMDS
X
Yusuke Iwama, Takahiro Noro, Kentaro Okano,
Hidetsura Cho,* and Hidetoshi Tokuyama*
THF
1445
Nitrosation Reaction
Acridone
Anthrone
NOH
47-97%
X = O, S, NBoc, NMe, CH2
Oxime
X
Xanthone
Synthesis of Pyrrolidine 3,4-Diol Derivatives with
Anticancer Activity on Pancreatic Tumor Cells
Frederic Steimer, Ana T. Carmona, Antonio J. Moreno-Vargas,
Irene Caffa, Michele Cea, Fabrizio Montecucco,
Alessio Nencioni, Pierre Vogel, and Inmaculada Robina*
H
N
HO
(.2 HCl)
(.2 HCl)
H
N
OH
HO
C6H4-p-CF3
!-mannosidase
"-Mannosidase Inhibitor
Pancreatic Cancer Cell
Pyrrolidine
Biphenyl Derivative
Iminosugar
H
N
H
N
OH
OH
OH
C6H4-p-CF3
pancreatic
cancer cells
1465
Advances in Siloxane-Based Coupling Reactions: Novel
16-Electron Palladium(0) Tri-alkene Catalysts for
Allyl-Aryl Coupling in Precursors to Amaryllidaceae
Alkaloids
Si(OEt)3
Pd(0)
Frederick E. Nytko, III, Krupa H. Shukla, and Philip DeShong*
Pd
O
OCO2Et
O
O
X
R
Pd
R
R
R
O
novel Pd(0) catalysts
Hiyama-like Coupling Reaction
1477
Allyl-Aryl Coupling Reaction
Amaryllidaceae Alkaloid
R
Bi(OTf)3 as a Dual Role Catalyst. Synthesis of Substituted
Morpholine Derivatives via Catalytic O-Allylation
TsN
16-Electron Palladium(0) Catalyst
R
OTBS
Bi(OTf)3 (cat)
TsN
Ryuji Hayashi, Jin-A Park, and Gregory R. Cook*
Bi(OTf)3
halide activation
Bi(OTf)3/H2O
desilylation
H
R
Ts
TfO
O
N
H
Bi(OTf)3
Dual Role Catalyst
Morpholine Derivative
O
X
Allylic Substitution Reaction
R
X
Bi
Ts
OTf
H
O
Bi
N
favored
OTf
X
OTf
H
Halide Activation
■ SHORT PAPERS
1491
Selective Preparation of 6- and 7-(Polyhydroxypropyl)pterins from Pentos-2-uloses
Tadashi Hanaya* and Kasumi Ito
1)
O
iPr
2Si
O
iPr Si
2
Pteridine
1501
Biopterin
Neopterin
Gabriel-Isay Condensation Reaction
O
N
NH2
O
NH2
O
N
AcHN
SiiPr2
O SiiPr2
N
HN
MeOH-H2O, NaHCO3, reflux
2) Ac2O, Py
O
O
O
OAc
N
O
O
O
H2N
OH
O
O
HN
same as above
OH
N
AcHN
O
OAc
N
HN
N
O
O
Pentos-2-ulose
Constituents from the Rhizomes of Curcuma comosa
and Their Wnt Signal Inhibitory Activities
Rolly G. Fuentes, Kazufumi Toume, Midori A. Arai,
Takashi Koyano, Thaworn Kowithayakorn, and
Masami Ishibashi*
O
O
HO
Wnt Signaling Pathway
Curcuma comosa
Diarylheptanoid
OH
OH
OH
MeO
OH
HO
OH
OMe
1511
Synthesis of 1,4-Disubstituted 1,2,3-Trizazoles via
Click Reaction in Micro Flow Reactor
Br
Ming Lei,* Ruijun Hu, Yanguang Wang, and Hong Zhang
+
R1
R2
R1
in MeCN
N
in H2O
1519
Click Reaction
12 examples
85-95% isolated yield
Microfluidic Chip Reactor
Iodoetherification of Conformationally Restricted Dienyl
Alcohols: Unexpected Formation of Oxocenes by 8-endomode Oxacyclizations
Me
Me
O
O
Kristen L. Stoltz, Andrea-Nekane R. Alba,
Frank E. McDonald,* Marika B. Wieliczko, and John Bacsa
1527
Iodoetherification Reaction
Oxacyclization Reaction
O
I2
Me NaHCO
3
HO
Dienyl Alcohol
N
R2
CuI + Na ascorbate + NaN3
1,4-Disubstituted 1,2,3-Trizazole
N
Oxocene
Me
Me
O
I
O
Me
Regioselectivity
Synthetic Studies on Furanosteroids. Functionalization
of Ring A of the Viridin Core Skeleton
Kristen C. Mascall and Peter A. Jacobi*
HO
HO
HO
NaHCO3, DMSO
NBS, AIBN
O
CCl4/CH2Cl2
Br
O
O
O
O
O
O
demethoxyviridin model
Viridin
1539
Furanosteroid
Bis-Heteroannulation Reaction
Kornblum Oxidation
Facile Formation of Imidazolinium Salt by Reaction of
Corresponding Diamine and Trimethyl Orthoformate in
1,1,1,3,3,3-Hexafluoroisopropanol
N
Kensuke Usui and Masahisa Nakada*
N
N
X
O
N
N
(X = BF4) 79%
(X = Cl)
73%
N-Heterocyclic Carbene
1553
Pincer Ligand
C2 Symmetric Ligand
Imidazolinium Salt
N
X
O
N
N
(X = BF4) 59%
(X = Cl) 73%
HFIP
Yb(OTf)3-Mediated Ring Opening of Functionalized
Cyclopentane Epoxides with Aniline: Aspects of
Regiochemistry and Stereochemistry
Stephen Hanessian* and Changwei Mu
OBn
OH
H
N
TBDPSO
Cyclopentane
Oxazoline
Azide
Ether
OBn
HN
OH
TBDPSO
1565
o-Directed Lithiation of Acylated Hydroxythiophenes
O
Ineta Vendina, Anete Parkova, and Peteris Trapencieris*
O
S
O
NEt2
O
S
NEt2
O
O
O
O
NEt2
NEt2
S
R
S
R = Me, SMe, SiMe3
2-Hydroxythiophene
1573
3-Hydroxythiophene
Directed ortho-Lithiation
Deprotonation
Preparation of New Heptafulvenes and the Related
Compounds Derived from 2H-Cyclohepta[d ]thiazol-2-one
and -2-thione
Ohki Sato,* Nobuhiro Ando, and Tatsuro Toma
S
S
MeO2C
N
H
1) CH2(CO2Me)2/NaH
X
N
MeO2C
1581
2H-Cyclohepta[d ]thiazol-2-thione
Dimethyl Malonate
Rare Earth Triflates/Chlorotrimethylsilane-Promoted
One-Pot Synthesis of Enals
X
Natsuko Kagawa, Yoshiko Sasaki, Shoko Sakaguchi,
Ayumi Nagatomo, Hideo Kojima, and Masahiro Toyota*
m
1587
Rare Earth Metal Triflate
Chlorotrimethylsilane
Heptafulvene
S
MeO2C
N
CO2Me
MeO2C
X
m
BzO
BzO
OBz
O
R
CHO
n
moderate yields
HO
O
OBz
O
BzO
BzO
Se
BzO
O
O
BzO
for PNB: IBr-AgClO4, MeOTf
for Bn : IBr-AgClO4
for PMB: In(OTf)3, (CuOTf)2•PhMe
Carbohydrate
OH
Development of a New Synthetic Strategy for Procyanidin
Dimer Condensation Using Peracetylated Electrophiles
Sayaka Ishihara, Syoma Doi, Kota Harui, Taisuke Okamoto,
Shuhei Okamoto, Joji Uenishi, Takashi Kawasaki,
Noriyuki Nakajima,* and Akiko Saito*
OAc
O
AcO
OAc
OAc
HO
O
OH
OH
OH
OH
O
HO
OH
OAc
OH
(-)-epicatechin peracetate
OH
procyanidin B1
Condensed Tannin
Oligomeric Flavonoid
2
Thiazole
n
R = NO2 (PNB)
R = H (Bn)
R = OMe (PMB)
1595
2
S
One-Pot Synthesis
Masanori Menjo, Hideki Tamai, Hiromune Ando,*
Hideharu Ishida, Mamoru Koketsu, and Makoto Kiso*
Selenoglycoisde
N
S
one-pot
CHO
Glycosidation Reactions of Benzyl-Type Selenoglycoside
Donors
Glycosidation Reaction
O
MeO2C
S
MeO2C
m=0, 1; n=0, 1; X=O, N, S
Enal
O
N
2) DDQ
X = O, S
2H-Cyclohepta[d ]thiazol-2-one
S
O
Flavan-3-ol Peracetate
Oligomer Synthesis
Lewis Acid Mediated Coupling Reaction
1603
Introducing the Diels-Alder Reactivity of 2Furanmethanethiol with Selected Maleic Acid
Derivatives
O
O
Mohanad Gh. Shkoor, Irena Nikoloska, and Adrian L. Schwan*
HS
O
+
O
H
H O
RS
O
CO2H
O
O
S
O
Diels-Alder Cycloaddition Reaction
1615
Conjugate Addition Reaction
Aromatization Reaction
Thiophthalide
Palladium-Catalyzed Cross-Coupling Reaction of
Trialkylbismuthines with 2-Haloazines and Diazines
Pauline Petiot and Alexandre Gagnon*
GF
Maleic Acid Derivative
R3Bi
N
N
Pd(0)
X
1625
Azine
Diazine
Cross-Coupling Reaction
Alkyl Coupling Reaction
Acid-Promoted Aromatization of Perylene-Based
Endoxides
Alejandro Criado, Manuel Vilas-Varela, Agustín Cobas,
Dolores Pérez, Diego Peña, and Enrique Guitián*
Reduction
Endoxide
Perylene
EtOH
O
Tol
Aromatization Reaction
HCl
H
O
1633
H
O
Tol
Tol
Tol
Carbenium Ion
Synthesis and Properties of Conducting Polymer
Nanotubes with Redox-Active Tetrathiafulvalene
Shinya Nambu, Tsukasa Nakahodo, and Hisashi Fujihara*
Tetrathiafulvalene
1639
N
Polythiophene
Nanotube
Redox-Active Compound
Regio- and Enantioselective Nitrone Cycloaddition
to Alkynones for the Synthesis of "4-Isoxazolines
Mukund P. Sibi,* Kelsey L. Dunkle, and Digamber Rane
S
S
S
S
S
S
S
S
S
S
S
S
S
S
Template Synthesis
O
N
N
O
Ph
N
Bn
Zn(Otf)2
4Å MS, CH2Cl2
-40 ºC
Z = template
O
Dipolar Cycloaddition Reaction
Enantioselective Reaction
Isoxazoline
Alkynone
N
O
Z
Ph
O
N
Nitrone
R
R = primary
alkyl group
X = Cl, Br, OTf
Organobismuthine
N
GF
O
N
Bn
1649
A Formal PCB-Free Synthesis of (-)-GSK1360707
via a Double Alkylation Reaction
Cl
Cl
Cl
Cl
Vassil I. Elitzin, Matthew J. Sharp, and Elie A. Tabet*
Cl
CO2Et
O
Lactam
1655
Alkylation Reaction
Enecarbamate Ester
Cl
1- LiHMDS
CH2ICl
CO2Et
N
N
H
GSK1360707
Boc
Alkyl Halide
H
N
Gerhard Laus, Sven Nerdinger,* Volker Kahlenberg, and
Herwig Schottenberger
N
six steps
N
H
1661
ortho-Lithiation
Asymmetric Alkylation of #-Cyanosulfones
Catalyzed by Chiral 1,2,3-Triazolium Salts
Kohsuke Ohmatsu, Yusuke Hakamata, Ayano Goto, and
Takashi Ooi*
O
O
OH
N
Electrophilic Azidation Reaction
N
Boc
Improved Synthesis of Antipsychotic Drug Bifeprunox
Antipsychotic Activity
CO2Et
2- LiHMDS
DMPU
N
Crystal Structure
NC
SO2i-Pr
R1
+
R2
Br
1·Br (3 mol%)
base (1.2 equiv)
mesitylene
(2 equiv)
NC
R1
c-Hex
SO2i-Pr
R2
up to 99% yield
er = up to 94.5:5.5
R
N
N
Ar'
Ar'
N
N
H H
Ph
Br
1·Br
"-Chiral Sulfonyl Compound
■ INDEXES
1667
1687
Author Index
Subject Index
1,2,3-Triazolium Ion
Phase-Transfer Catalyst
Alkylation Reaction
Tetrasubstituted Chiral Carbon Center
O
Ar
Contributors
To This Issue
1213
Abel, Anton S.
1121
Fukuda, Tsutomu
1255
Adams, David R.
1615
Gagnon, Alexandre
1135
Aitken, R. Alan
1101
Gnanaprakasam, Boopathy
1519
Alba, Andrea-Nekane R.
1661
Goto, Ayano
1625
Guitián, Enrique
939 Albert, Vincent
1079
Alker, André M.
1661
Hakamata, Yusuke
1587
Ando, Hiromune
1323
Hamada, Tomohito
1573
Ando, Nobuhiro
1355
Hamanaka, Risa
1337
Ando, Shin
1371
Hamashima, Yoshitaka
1501
Arai, Midori A.
1491
Hanaya, Tadashi
1371
Asakawa, Tomohiro
1553
Hanessian, Stephen
1201
Hara, Shoji
1595
Harui, Kota
969 Asakura, Hiroki
1213
Averin, Alexei D.
1311
Baba, Ayana
1079
Bach, Thorsten
1477
Hayashi, Ryuji
1519
Bacsa, John
1323
Hayashi, Tatsuya
1191
Baire, Beeraiah
1299
He, Zhi
1135
Barker, Graeme
1101
Heidemann, Sven
1311
Hideshima, Kumiko
827 Barl, Nadja M.
961 Hashimoto, Ryota
1213
Beletskaya, Irina P.
1101
Hierold, Judith
1213
Bessmertnykh-Lemeune, Alla
1175
Higashiyama, Kimio
1371
Hiza, Aiki
953 Bingham, Matilda
939 Boukouvalas, John
975 Honzawa, Shinobu
1445
Caffa, Irene
1175
Horikoshi, Hiroki
1445
Carmona, Ana T.
1191
Hoye, Thomas R.
1445
Cea, Michele
1233
Hsung, Richard P.
1299
Chen, Gang
1511
Hu, Ruijun
1191
Chen, Junhua
1255
Hudlicky, Jason R.
1255
Hudlicky, Tomas
1287
Iida, Keisuke
945 Chiba, Yuna
1433
Cho, Hidetsura
1135
Cleghorn, Lee P.
1625
Cobas, Agustín
1477
Cook, Gregory R.
1625
Criado, Alejandro
1501
Ishibashi, Masami
1213
Denat, Franck
1587
Ishida, Hideharu
1465
DeShong, Philip
1595
Ishihara, Sayaka
1065
Ding, Jie
1051
Ishikawa, Kyoko
1595
Doi, Syoma
1337
Ishimoto, Naoko
1149
Dörr, Aurélie A.
1337
Ishizuka, Tadao
1039
Doyle, Michael P.
1491
Ito, Kasumi
1639
Dunkle, Kelsey L.
1649
Elitzin, Vassil I.
1121
Itoyama, Ryosuke
997 Endo, Yasuyuki
1433
Iwama, Yusuke
961 Iida, Toshiaki
1371
Inai, Makoto
997 Inomata, Kohei
961 Itoh, Yoshimitsu
1337
Eshita, Iori
1121
Iwao, Masatomo
1065
Fan, Wei
1101
Jackenkroll, Stefan
1079
Fort, Diego A.
1527
Jacobi, Peter A.
1163
Foubelo, Francisco
1233
Fox, Sierra K.
1065
Jiang, Bo
1501
Fuentes, Rolly G.
1013
Justino, Jorge
1633
Fujihara, Hisashi
1051
Fujii, Hideaki
1581
Kagawa, Natsuko
1323
Fujioka, Hiromichi
1655
Kahlenberg, Volker
945 Fujiwara, Kenshu
1371
Kan, Toshiyuki
1355
Fukai, Miku
981 Järving, Ivar
969 Kadota, Isao
919 Kanai, Motomu
1355
1445
Nencioni, Alessio
1639
Sibi, Mukund P.
945 Katoono, Ryo
Kanda, Kazumasa
1655
Nerdinger, Sven
1013
Silva, Filipa V. M.
945 Kawai, Hidetoshi
1603
Nikoloska, Irena
1013
Silva, Sandrina
1595
Kawasaki, Takashi
1433
Noro, Takahiro
1397
Kelzhanova, Nazken
1465
Nytko, III, Frederick E.
1163
Sirvent, Juan A.
1587
Kiso, Makoto
1275
O'Doherty, George A.
1445
Steimer, Frederic
1323
Kita, Yasuyuki
1371
Ogawa, Takahiro
1519
Stoltz, Kristen L.
827 Knochel, Paul
1661
Ohmatsu, Kohsuke
975 Sugihara, Takumichi
1581
Kojima, Hideo
1587
Koketsu, Mamoru
1175
Okamoto, Kenya
1501
Kowithayakorn, Thaworn
1595
Okamoto, Shuhei
1649
Tabet, Elie A.
1501
Koyano, Takashi
1595
Okamoto, Taisuke
1311
Tabuchi, Yuri
1175
Kudo, Shintaro
1433
Okano, Kentaro
911 Takahashi, Hiroki
1323
Kurachi, Takeshi
1323
Oki, Tomohiro
969 Takamura, Hiroyoshi
1397
Langer, Peter
1661
Ooi, Takashi
945 Takeda, Takashi
1655
Laus, Gerhard
1355
Oshima, Shoya
1511
Lei, Ming
1065
Li, Guigen
899 Li, Yang
981 Lopp, Margus
1149
Lubell, William D.
981 Lumi, Priit
981 Oja, Karolin
879 "imánek, Vilím
981 Paju, Anne
1477
Park, Jin-A
1565
Parkova, Anete
981 Pehk, Tõnis
1175
Sugiura, Takaya
945 Suzuki, Takanori
1175
Takidaira, Jun-ichi
911 Takimoto, Tatsuya
1587
Tamai, Hideki
911 Tamura, Rui
969 Tanaka, Tokihiro
1625
Peña, Diego
1013
Tatibouët, Arnaud
1625
Pérez, Dolores
1101
Tietze, Lutz F.
1233
Lv, Ming-Can
1615
Petiot, Pauline
1433
Tokuyama, Hidetoshi
1101
Ma, Ling
1397
Pfeiffer, Wolf-Diethard
1573
Toma, Tatsuro
1323
Maehata, Ryota
1233
Qi, Rui
1051
Tomatsu, Miyuki
1213
Maloshitskaya, Olga A.
1639
Rane, Digamber
1311
Tomioka, Kiyoshi
1039
Mandler, Michael D.
1013
Rauter, Amélia Pilar
1527
Mascall, Kristen C.
1135
Reid, Euan J.
1501
Toume, Kazufumi
1101
Reiner, Johannes R.
1581
Toyota, Masahiro
1135
Roberts, Sheryl S.
1565
Trapencieris, Peteris
1445
Robina, Inmaculada
1039
Truong, Phong M.
1287
Tsubouchi, Gen
981 Matkevit!, Katharina
1337
Matsunaga, Hirofumi
* McCubbin, Adam
961 Tomita, Yuichi
1519
McDonald, Frank E.
1013
Rollin, Patrick
1587
Menjo, Masanori
1397
Roßberg, Harald
1397
Saginayev, Amanzhan T.
1371
Tsukaguchi, Yuta
1595
Saito, Akiko
1337
Tsunoda, Shoichi
1065
Tu, Shu-Jiang
961 Mikami, Koichi
911 Tsue, Hirohito
1121
Minagawa, Terufusa
1311
Miyawaki, Akari
1175
Mizushima, Noriko
1445
Montecucco, Fabrizio
827 Sämann, Christoph
1595
Uenishi, Joji
1445
Moreno-Vargas, Antonio J.
911 Sasaki, Hideaki
1213
Uglov, Alexei N.
1539
Usui, Kensuke
953 Moutrille, Cécile
929 Saito, Nozomi
1581
Sakaguchi, Shoko
975 Uchida, Mitsuaki
1175
Sasaki, Shigeru
1553
Mu, Changwei
1581
Sasaki, Yoshiko
1323
Murai, Kenichi
1573
Sato, Ohki
1255
van Kempen, Johannes
1287
Nagasawa, Kazuo
929 Sato, Yoshihiro
1565
Vendina, Ineta
1051
Nagase, Hiroshi
1655
Schottenberger, Herwig
1625
Vilas-Varela, Manuel
1581
Nagatomo, Ayumi
1603
Schwan, Adrian L.
1397
Villinger, Alexander
1539
Nakada, Masahisa
1039
Shanahan, Charles S.
1445
Vogel, Pierre
1323
Nakahara, Kenji
1275
Sharif, Ehesan U.
1633
Nakahodo, Tsukasa
1649
Sharp, Matthew J.
1201
Wakita, Natshumi
1595
Nakajima, Noriyuki
1355
Shibata, Takanori
1029
Wang, Juanjuan
919 Shimizu, Yohei
1233
Wang, Xiao-Na
969 Shiroma, Kengo
1511
Wang, Yanguang
929 Nakamura, Ken-ichi
1287
Nakamura, Takahiro
1311
Nakano, Mai
1355
Shizuno, Tsubasa
1633
Nambu, Shinya
1603
Shkoor, Mohanad Gh.
845 Negishi, Ei-ichi
1465
Shukla, Krupa H.
879 Vacek, Jan
945 Wada, Kazuhisa
827 Werner, Veronika
899 White, James D.
1519
Wieliczko, Marika B.
1079
Woltering, Thomas J.
1029
Xu, Hui
845 Xu, Shiqing
1323
Yamakawa, Maki
1311
Yamamoto, Yasutomo
1175
Yamauchi, Takayasu
1029
Yan, Yuanyuan
919 Yasuda, Kouji
1299
Yudin, Andrei K.
1163
Yus, Miguel
953 Zard, Samir Z.
879 Zatloukalová, Martina
1511
Zhang, Hong
1065
Zhang, Jin-Peng
1213
Zubrienko, Georgii A.
*Frontispiece Drawing

htr_main (jielde)

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