smo_main (kewpie2)

HETEROCYCLES, Vol. 81, No. 2, 2010
■ REVIEW
259
Total Synthesis of Strychnine
N
Miwako Mori*
H
N
H
O
H
H
O
H
(-)-strychnine
Strychnine
Palladium Catalyzed Cyclization
Tubifoline
Asymmetric Allylic Substitution
Heck Reaction
■ PAPERS
293
Stereoselective Intramolecular Cyclization of Isopentenyl
Benzamide via -Allylpalladium Complex Catalyzed by
Pd(0)
OAc
3 steps
TBSO
OH
NHBz
TBSO
NHBz
74%
Jae-Eun Joo, Yu Mu, Yiu-Suk Lee, Yong-Shou Tian,
Gyu-Jin Lee, and Won-Hun Ham*
TBSO
3 steps
N
Pd(PPh3)4
K2CO3, MeCN
ref.
MeO2C
N
O
O
69%
Ph
Ph
Stereoselective Synthesis
305
Chiral Oxazoline
Palladium
Catalysis
Lactacystin
From 2,3-, 2,6-, 3,4- and 4,6-Dichloroquinolines to Isomeric
Chloroquinolinesulfonyl Chlorides
4
6
x-Cl
7
Krzysztof Marciniec* and Andrzej Malankiewicz
N
y-SO2Cl
x-Cl
3
y-Cl
2
y-Cl
x-ClO2S
N
N
(x=6,7; y=2 or 4)
Sulfonamide
317
Sulfonyl Chloride
Quinoline
Oxidative Chlorination of Quinolinyl Sulfide
(x=3,6,7; y=2 or 4)
Nucleophilic Heteroaromatic Substitution
One-Pot Aryl-1,4-thiomorpholine 1,1-Dioxide Synthesis
via Double 1,4-Addition of in situ Reduced Nitroarenes
to Divinyl Sulfones
Joon Hee Han, Jaehwan Choi, Young Moo Jun,
Byung Min Lee, and Byeong Hyo Kim*
Heterocyclization
Indium
Divinyl Sulfone
Nitroarene
Ar NO2
2
Aza-Michael Type Addition
SO2
In, AcOH
MeOH—sat-aq. NH4Cl
or MeOH, ref.
Ar N
SO2
HETEROCYCLES, Vol. 81, No. 2, 2010
329
Cyclization of 5-Cyano-6-cyanoimino-3,4-dihydropyridin2(1H)-ones with Amines
Núria Mont, Francisco Carrión, José I. Borrell,* and
Jordi Teixidó
O
H
N
N
R1
1,5-Dinitrile
349
Cyclization
Amine
Pyrido[2,3-d]pyrimidine
CN
7{1-4}
CN
R2
R1
4{1-2}
4{1} H Me
4{2} Me H
H
N
O
NHR3R4
NR3R4 O
N
R2
R2
5{x,y}
H
N
NR3R4
+
N
R1
NH2
O
NH2
N
+
N
R1
R2
H
N
R1
CN
R2
NR3R4
6{x,y}
8{x,y}
Mechanism
Facile Synthesis of 3-Methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl and Derivatives
O
CO2R
Bunpei Hatano,* Hiroki Araya, Yutaka Yoshimura,
Haruna Sato, Tomohiro Ito, Tateaki Ogata, and
Tatsuro Kijima
R=H
R = Me
R = Et
R= iso-Pr
N
N
H
O
total 54 - 65% yields (4 or 5 steps)
3-Methoxycarbonyl- and 3-Carbonyl-2,2,5,5-tetramethylpyrrolidine-1-oxyls
357
Favorskii Rearrangement
A Concise Synthesis of Fluorine-Containing Benzo[h]quinolines and Benzo[h]quinolones by Selective
Pyridine and Pyridinone Rings Formation Reactions
of N-Propargyl-2,4-bis(trifluoroacetyl)-1-naphthylamine
with Various Active Methylene Compounds
Spine Probe
ref.
R1CH(CO2R2)2
R2ONa
COCF3
COCF3
O
COCF3
OH
CF3
-20 °C or
N
SOCl2
pyridine
CO2R2
CF3
0 °C
30 °C
R3COCH2COR4
EtONa
COR3(R4)
N
COCF3
COCF3
(R1, R2) = (H, Me), (H, Et), (H, iso-Pr), (H, tert-Bu), (Me, Et)
(R3, R4) = (Me, Me), (Ph, Ph), (Me, Ph)
N-Propargyl-1-naphthylamine
Fluorine Compound
Active Methylene Compound
Synthesis of a 6H-Chromeno[3,4-b]quinoline and
a 6a,12a-Dehydro-7-azarotenoid
O
Andrew L. C. Morris and Yvette A. Jackson*
Cl
MeO
MeO
N
H
Palladium-Mediated Reaction
381
O
CO2R2
N
COCF3
371
R1
CO2R2
CF3
30 °C or
HN
CF3
1H-Benzo[h]quinolin-2-one
CO2R2
N
Etsuji Okada,* Dai Shibata, Norikado Tsukushi,
Masato Dohura, Norio Ota, Satoru Adachi, and
Maurice Médebielle
Benzo[h]quinoline
Nitroxyl Radical
Heck Reaction
Rotenoid
Me
N
Aza Derivative
Synthesis of 20-Epi-eldecalcitol [20-Epi-1,25-dihydroxy2-(3-hydroxypropoxy)vitamin D3: 20-Epi-ED-71]
20
OH
Madoka Yoshino, Kohei Eto, Keisuke Takahashi,
Jun Ishihara, Susumi Hatakeyama, Yoshiyuki Ono,
Hitoshi Saito, and Noboru Kubodera*
HO
OH
O
OH
20-epi-eldecalcitol
Calcitriol
Eldecalcitriol
20-Epi-Calcitriol
20-Epi-Eldecalcitol
Trost Coupling Reaction
O
HETEROCYCLES, Vol. 81, No. 2, 2010
■ NOTES
395
Me
Me
Synthesis of Some New Pyridazinylspirohetarylindoles
and Hetarylpyridazine Derivatives
Yassin Gabr,* Mohamed Abdel-Megid,
Mohamed Abdel-Hamid Awas, and
Naser Mohamed Abdel-Fatah
Ph N NH
Ph
O
Ph O
Ph
NH
N
N
O
O
N
H
Me
N
H
Me
N
H
O
O
N2H4. H2O
O
O
Ph
O
Ph
NH
N
O
N
H
NH
O
N
H
H2 N
NH2
S
NH2
S
Ph
407
Hetarylpyridazine
NH2
N
H
O
NH2
HN
Ph N N
Ph
NH
N
Pyridazinyl Spirohetarylindole
N
H
H2 N
Ph N N
NH
N
O
N
H
O
O
Substituted Thiazine
15
N NMR Spectroscopy of Annulated 2-Pyrazolines and
2-1,2,4-Triazolines
Teresa Recca, Lara De Benassuti, and Giorgio Molteni*
Annulated 2-Pyrazoline
413
Annulated 2-1,2,4-Triazoline
15
N Chemical Shift
INEPT Experiment
S-Methylation of N-Containing Heterocyclic Thiols
with Conjugated Acids of Methoxy Groups
HMBC Experiment
MeOH
Masao Shimizu,* Teruaki Shimazaki, Yoshihiro Kon,
and Takeo Konakahara
or MeOR
or (MeO)2CO
N
H+
SH
N
Me
S
SN2cA mechanism
S-Alkylation
421
Pyridinethiol
Alcohol
Conjugated Acid
SN2cA Reaction
Ph
Synthesis of Optically Active -Valerolactone and
-Nonanolactone via Optical Resolution Using Chiral
Amine Derived from Amino Acid
Kenichi Yumoto, Morifumi Hasegawa, and Hiroaki Toshima*
Ph
O
R
H
N
O
R
O
O
R
O
O
NH2
O
1) ring opening amidation of -lactones; 2) optical resolution
by fractional crystallization; 3) hydrolysis
-Lactone
433
Optical Resolution
Amino Acid Derivative
Chiral Amine
L-Phenylalanine
Synthesis of 1-(1-Arylsulfanylalkyl)indoles and
2,2-Bis[1-(1-arylsulfanylalkyl)indol-3-yl]propanes
by Acid-Catalyzed Reactions of Indoles with Aryl
Vinyl Sulfides
Kazuhiro Kobayashi,* Yuu Shirai, Shuhei Fukamachi,
and Hisatoshi Konishi
R1
R1
R2
Indole
Bis(indol-3-yl)methane
Acid-Catalyzed Reactioin
R2
N
Me
Vinyl Sulfide
cat. CSA
R2
N
H
= alkyl
cat. CSA
R2 = H
Me
R1
N
SAr
Me
SAr
Me
(±)-Camphor-10-sulfonic Acid
Me
Me
R1
N
Me
Me Me
SAr
SAr
HETEROCYCLES, Vol. 81, No. 2, 2010
441
Cephastigiamide A, and Antiplasmodial Activity
of Cephalotaxus Alkaloids from Cephalotaxus
harringtonia forma fastigiata
Hiroshi Morita,* Yuta Nagakura, Takahiro Hosoya,
Wiwied Ekasari, Aty Widyawaruyanti,
Kanami Mori-Yasumoto, Setsuko Sekita, and
Yusuke Hirasawa
O
N
OH
MeO2C
OH
O
HO
OMe
O
cephastigiamide A (1)
Cephastigiamide A
Alkaloid
Cephalotaxus harringtonia forma fastigiata
■ NEW HETEROCYCLIC NATURAL PRODUCTS
451
453
463
481
487
493
Polyketides
Aromatics
Terpenes
Steroids
Alkaloids
Miscellaneous
■ TOTAL SYNTHESIS OF HETEROCYCLIC NATURAL PRODUCTS
495
501
505
507
Polyketides
Aromatics
Terpenes
Alkaloids
Antiplasmodial Activity
O
HETEROCYCLES, Vol. 81, No. 2, 2010
Contributors
To This Issue
395 Abdel-Fatah, Naser Mohamed
441 Sekita, Setsuko
395 Abdel-Megid, Mohamed
357 Shibata, Dai
357 Adachi, Satoru
413 Shimazaki, Teruaki
349 Araya, Hiroki
413 Shimizu, Masao
395 Awas, Mohamed Abdel-Hamid
433 Shirai, Yuu
329 Borrell, José I.
381 Takahashi, Keisuke
329 Carrión, Francisco
329 Teixidó , Jordi
317 Choi, Jaehwan
293 Tian, Yong-Shou
407 De Benassuti, Lara
421 Toshima, Hiroaki
357 Dohura, Masato
357 Tsukushi, Norikado
441 Ekasari, Wiwied
441 Widyawaruyanti, Aty
381 Eto, Kohei
349 Yoshimura, Yutaka
433 Fukamachi, Shuhei
381 Yoshino, Madoka
395 Gabr, Yassin
421 Yumoto, Kenichi
293 Ham, Won-Hun
317 Han, Joon Hee
421 Hasegawa, Morifumi
381 Hatakeyama, Susumi
349 Hatano, Bunpei
441 Hirasawa, Yusuke
441 Hosoya, Takahiro
381 Ishihara, Jun
349 Ito, Tomohiro
371 Jackson, Yvette A.
293 Joo, Jae-Eun
317 Jun, Young Moo
349 Kijima, Tatsuro
317 Kim, Byeong Hyo
433 Kobayashi, Kazuhiro
413 Kon, Yoshihiro
413 Konakahara, Takeo
433 Konishi, Hisatoshi
381 Kubodera, Noboru
317 Lee, Byung Min
293 Lee, Gyu-Jin
293 Lee, Yiu-Suk
305 Marciniec, Krzysztof
305 Malankiewicz, Andrzej
357 Médebielle, Maurice
407 Molteni, Giorgio
329 Mont, Núria
259 Mori, Miwako
441 Morita, Hiroshi
441 Mori-Yasumoto, Kanami
371 Morris, Andrew L. C.
293 Mu, Yu
441 Nagakura, Yuta
349 Ogata, Tateaki
357 Okada, Etsuji
381 Ono, Yoshiyuki
357 Ota, Norio
407 Recca, Teresa
381 Saito, Hitoshi
349 Sato, Haruna