共 9 条
Anodic oxidation reactions: the total synthesis of (+)-nemorensic acid
被引:14
作者:

Liu, B
论文数: 0 引用数: 0
h-index: 0
机构:
Washington Univ, Dept Chem, St Louis, MO 63130 USA Washington Univ, Dept Chem, St Louis, MO 63130 USA

Moeller, KD
论文数: 0 引用数: 0
h-index: 0
机构:
Washington Univ, Dept Chem, St Louis, MO 63130 USA Washington Univ, Dept Chem, St Louis, MO 63130 USA
机构:
[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA
基金:
美国国家卫生研究院;
美国国家科学基金会;
关键词:
D O I:
10.1016/S0040-4039(01)01506-4
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The anodic coupling of an enol ether to an oxygen nucleophile has been used as a key step in the total synthesis of (+)-nemorensic acid. The anodic cyclization reaction allows for a reversal in the way the tetrahydrofuran ring of the natural product is normally assembled and thus enables construction of the ring in a highly stereoselective fashion. (C) 2001 Elsevier Science Ltd. All rights reserved.
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页码:7163 / 7165
页数:3
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[1]
SYNTHESES WITH SULFONES .49. STEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (S)-(-)-3,9-DIMETHYL 6-(1-METHYLETHYL) (E)-5,8-DECADIEN-1-OL ACETATE, SEXUAL PHEROMONE OF YELLOW SCALE
[J].
ALVAREZ, E
;
CUVIGNY, T
;
DUPENHOAT, CH
;
JULIA, M
.
TETRAHEDRON,
1988, 44 (01)
:119-126

ALVAREZ, E
论文数: 0 引用数: 0
h-index: 0
机构:
ECOLE NORMALE SUPER,CHIM LAB,24 RUE LHOMOND,F-75231 PARIS 05,FRANCE ECOLE NORMALE SUPER,CHIM LAB,24 RUE LHOMOND,F-75231 PARIS 05,FRANCE

CUVIGNY, T
论文数: 0 引用数: 0
h-index: 0
机构:
ECOLE NORMALE SUPER,CHIM LAB,24 RUE LHOMOND,F-75231 PARIS 05,FRANCE ECOLE NORMALE SUPER,CHIM LAB,24 RUE LHOMOND,F-75231 PARIS 05,FRANCE

DUPENHOAT, CH
论文数: 0 引用数: 0
h-index: 0
机构:
ECOLE NORMALE SUPER,CHIM LAB,24 RUE LHOMOND,F-75231 PARIS 05,FRANCE ECOLE NORMALE SUPER,CHIM LAB,24 RUE LHOMOND,F-75231 PARIS 05,FRANCE

JULIA, M
论文数: 0 引用数: 0
h-index: 0
机构:
ECOLE NORMALE SUPER,CHIM LAB,24 RUE LHOMOND,F-75231 PARIS 05,FRANCE ECOLE NORMALE SUPER,CHIM LAB,24 RUE LHOMOND,F-75231 PARIS 05,FRANCE
[2]
Anodic electrochemistry and the use of a 6-volt lantern battery: A simple method for attempting electrochemically based synthetic transformations
[J].
Frey, DA
;
Wu, N
;
Moeller, KD
.
TETRAHEDRON LETTERS,
1996, 37 (46)
:8317-8320

Frey, DA
论文数: 0 引用数: 0
h-index: 0
机构:
WASHINGTON UNIV,DEPT CHEM,ST LOUIS,MO 63130 WASHINGTON UNIV,DEPT CHEM,ST LOUIS,MO 63130

Wu, N
论文数: 0 引用数: 0
h-index: 0
机构:
WASHINGTON UNIV,DEPT CHEM,ST LOUIS,MO 63130 WASHINGTON UNIV,DEPT CHEM,ST LOUIS,MO 63130

Moeller, KD
论文数: 0 引用数: 0
h-index: 0
机构:
WASHINGTON UNIV,DEPT CHEM,ST LOUIS,MO 63130 WASHINGTON UNIV,DEPT CHEM,ST LOUIS,MO 63130
[3]
Enantiospecific synthesis of (+)-nemorensic acid, a necic acid component of the macropyrrolizidine alkaloid, nemorensine
[J].
Honda, T
;
Ishikawa, F
.
JOURNAL OF ORGANIC CHEMISTRY,
1999, 64 (15)
:5542-5546

Honda, T
论文数: 0 引用数: 0
h-index: 0
机构:
Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan

Ishikawa, F
论文数: 0 引用数: 0
h-index: 0
机构:
Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan
[4]
CHIRAL SYNTHESIS VIA ORGANOBORANES .5. ASYMMETRIC ALLYLBORATION VIA CHIRAL ALLYLDIALKYLBORANES - SYNTHESIS OF HOMOALLYLIC ALCOHOLS WITH EXCEPTIONALLY HIGH ENANTIOMERIC EXCESS
[J].
JADHAV, PK
;
BHAT, KS
;
PERUMAL, PT
;
BROWN, HC
.
JOURNAL OF ORGANIC CHEMISTRY,
1986, 51 (04)
:432-439

JADHAV, PK
论文数: 0 引用数: 0
h-index: 0
机构:
PURDUE UNIV,RICHARD B WETHERILL LAB CHEM,W LAFAYETTE,IN 47907 PURDUE UNIV,RICHARD B WETHERILL LAB CHEM,W LAFAYETTE,IN 47907

BHAT, KS
论文数: 0 引用数: 0
h-index: 0
机构:
PURDUE UNIV,RICHARD B WETHERILL LAB CHEM,W LAFAYETTE,IN 47907 PURDUE UNIV,RICHARD B WETHERILL LAB CHEM,W LAFAYETTE,IN 47907

论文数: 引用数:
h-index:
机构:

BROWN, HC
论文数: 0 引用数: 0
h-index: 0
机构:
PURDUE UNIV,RICHARD B WETHERILL LAB CHEM,W LAFAYETTE,IN 47907 PURDUE UNIV,RICHARD B WETHERILL LAB CHEM,W LAFAYETTE,IN 47907
[5]
PYRROLIZIDINE ALKALOIDS .20. NEMORENSINE, AN ALKALOID FROM SENECIO-NEMORENSIS L
[J].
KLASEK, A
;
SEDMERA, P
;
BOEVA, A
;
SANTAVY, F
.
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS,
1973, 38 (08)
:2504-2512

KLASEK, A
论文数: 0 引用数: 0
h-index: 0
机构: PALACKY UNIV, MED FAC, INST CHEM, 775 15 OLOMOUC, CZECHOSLOVAKIA

SEDMERA, P
论文数: 0 引用数: 0
h-index: 0
机构: PALACKY UNIV, MED FAC, INST CHEM, 775 15 OLOMOUC, CZECHOSLOVAKIA

BOEVA, A
论文数: 0 引用数: 0
h-index: 0
机构: PALACKY UNIV, MED FAC, INST CHEM, 775 15 OLOMOUC, CZECHOSLOVAKIA

SANTAVY, F
论文数: 0 引用数: 0
h-index: 0
机构: PALACKY UNIV, MED FAC, INST CHEM, 775 15 OLOMOUC, CZECHOSLOVAKIA
[6]
TOTAL SYNTHESIS OF (+/-)-NEMORENSIC ACID
[J].
KLEIN, LL
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1985, 107 (08)
:2573-2574

KLEIN, LL
论文数: 0 引用数: 0
h-index: 0
[7]
Synthetic applications of anodic electrochemistry
[J].
Moeller, KD
.
TETRAHEDRON,
2000, 56 (49)
:9527-9554

Moeller, KD
论文数: 0 引用数: 0
h-index: 0
机构:
Washington Univ, Dept Chem, St Louis, MO 63130 USA Washington Univ, Dept Chem, St Louis, MO 63130 USA
[8]
Anodic cyclization reactions: Reversing the polarity of ketene dithioacetal groups
[J].
Sun, YM
;
Liu, B
;
Kao, J
;
d'Avignon, DA
;
Moeller, KD
.
ORGANIC LETTERS,
2001, 3 (11)
:1729-1732

Sun, YM
论文数: 0 引用数: 0
h-index: 0
机构:
Washington Univ, Dept Chem, St Louis, MO 63130 USA Washington Univ, Dept Chem, St Louis, MO 63130 USA

Liu, B
论文数: 0 引用数: 0
h-index: 0
机构:
Washington Univ, Dept Chem, St Louis, MO 63130 USA Washington Univ, Dept Chem, St Louis, MO 63130 USA

Kao, J
论文数: 0 引用数: 0
h-index: 0
机构:
Washington Univ, Dept Chem, St Louis, MO 63130 USA Washington Univ, Dept Chem, St Louis, MO 63130 USA

d'Avignon, DA
论文数: 0 引用数: 0
h-index: 0
机构:
Washington Univ, Dept Chem, St Louis, MO 63130 USA Washington Univ, Dept Chem, St Louis, MO 63130 USA

Moeller, KD
论文数: 0 引用数: 0
h-index: 0
机构:
Washington Univ, Dept Chem, St Louis, MO 63130 USA Washington Univ, Dept Chem, St Louis, MO 63130 USA
[9]
Reversing the polarity of enol ethers: An anodic route to tetrahydrofuran and tetrahydropyran rings
[J].
Sutterer, A
;
Moeller, KD
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000, 122 (23)
:5636-5637

Sutterer, A
论文数: 0 引用数: 0
h-index: 0
机构:
Washington Univ, Dept Chem, St Louis, MO 63106 USA Washington Univ, Dept Chem, St Louis, MO 63106 USA

Moeller, KD
论文数: 0 引用数: 0
h-index: 0
机构:
Washington Univ, Dept Chem, St Louis, MO 63106 USA Washington Univ, Dept Chem, St Louis, MO 63106 USA