The first enantiospecific total synthesis of the 3-oxygenated sarpagine indole alkaloids affinine and 16-epiaffinine, as well as vobasinediol and 16-epivobasinediol

被引：15
作者：
Yang, Jie [1 ]
Rallapalli, Sundari K. [1 ]
Cook, James M. [1 ]
机构：
[1] Univ Wisconsin, Dept Chem, Milwaukee, WI 53211 USA
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 05期
关键词：
ANTIMICROBIALLY ACTIVE ALKALOIDS; STEREOSPECIFIC TOTAL-SYNTHESIS; 2-ACYLINDOLE ALKALOIDS; GENERAL-APPROACH; PESCHIERA-FUCHSIAEFOLIA; VINBLASTINE DERIVATIVES; STRYCHNOS ALKALOIDS; CARBONYL-COMPOUNDS; CYCLIZATION; SKELETON;
D O I：
10.1016/j.tetlet.2009.12.002
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first enantiospecific total synthesis of the 3-oxygenated sarpagine indole alkaloids affinine (1) and 16-epiaffinine (2) as well as the synthesis of vobasinediol (3) and 16-epivobasinediol (4) was accomplished from D-(+)-tryptophan methyl ester. (c) 2009 Elsevier Ltd. All rights reserved.
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页码：815 / 817
页数：3
相关论文
共 54 条
[1]   CATHARINENSINE, AN OXINDOLE ALKALOID FROM PESCHIERA-CATHARINENSIS [J].
ARAUJO, AR ;
KASCHERES, C ;
FUJIWARA, F ;
MARSAIOLI, AJ .
PHYTOCHEMISTRY, 1984, 23 (10) :2359-2363
[2]   Synthesis of indoles via palladium[0]-mediated Ullmann cross-coupling of o-halonitroarenes with α-halo-enones or -enals [J].
Banwell, MG ;
Kelly, BD ;
Kokas, OJ ;
Lupton, DW .
ORGANIC LETTERS, 2003, 5 (14) :2497-2500
[3]   A novel route to the geissoschizine skeleton: The influence of ligands on the diastereoselectivity of the Heck cyclization [J].
Birman, VB ;
Rawal, VH .
TETRAHEDRON LETTERS, 1998, 39 (40) :7219-7222
[4]   STUDIES ON THE SYNTHESIS OF STRYCHNOS INDOLE ALKALOIDS - SYNTHESIS OF (+/-)-DEHYDROTUBIFOLINE [J].
BONJOCH, J ;
SOLE, D ;
BOSCH, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :11017-11018
[5]   A general synthetic entry to Strychnos alkaloids of the curan type via a common 3a-(2-nitrophenyl)hexahydroindol-4-one intermediate. Total syntheses of (+/-)- and (-)-tubifolidine, (+/-)-akuammicine, (+/-)-19,20-dihydroakuammicine, (+/-)-norfluorocurarine, (+/-)-echitamidine, and (+/-)-20-epilochneridine [J].
Bonjoch, J ;
Sole, D ;
GarciaRubio, S ;
Bosch, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (31) :7230-7240
[6]   Total syntheses of (±)-deethylibophyllidine using a crisscross annulation:: Ring cleavage of octahydroindolo[2,3-a]quinolizines followed by tandem cyclizations of octahydroazecino[5,4-b]indoles [J].
Bonjoch, J ;
Fernandez, JC ;
Valls, N .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7338-7347
[7]  
BRAGA RM, 1984, PHYTOCHEMISTRY, V23, P175, DOI 10.1016/0031-9422(84)83102-7
[8]   ALKALOIDS OF TABERNAEMONTANA-PSYCHOTRIFOLIA HBK [J].
BURNELL, RH ;
MEDINA, JD .
CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (02) :307-&
[9]   SELENIUM DIOXIDE OXIDATIONS IN THE INDOLE AREA - SYNTHESIS OF BETA-CARBOLINE ALKALOIDS [J].
CAIN, M ;
CAMPOS, O ;
GUZMAN, F ;
COOK, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (04) :907-913
[10]  
CAVA MP, 1964, CHEM IND-LONDON, P1193
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