CHIRAL TOTAL SYNTHESIS OF INDOLE ALKALOIDS OF THE ASPIDOSPERMA AND HUNTERIA TYPES

被引：130

作者：

NODE, M ^{[1
]}

NAGASAWA, H ^{[1
]}

FUJI, K ^{[1
]}

机构：

[1] KYOTO UNIV,INST CHEM RES,UJI,KYOTO 611,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 02期

关键词：

D O I：

10.1021/jo00289a025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Expeditious enantioselective syntheses of (+)~quebrachamine (6), (-)-aspidospermidine (7), (+)-demethoxy-aspidospermine (8), and (-)-eburnamonine (9) were accomplished starting from (S)-lactone 1. The syntheses also complete formal, total syntheses of 12 other indole alkaloids of the Aspidosperma and Hunteria types. The key step in the synthesis of (+)-quebrachamine (6) was the Pictet-Spengler condensation of chiral C9 unit 10, derived from 1, with tryptamine. Another C9 unit (15) was also prepared from 1 and utilized for the syntheses of three other alkaloids, 7, 8, and 9. © 1990, American Chemical Society. All rights reserved.

引用

页码：517 / 521

页数：5

共 70 条

[31]

IMANISHI T, 1982, CHEM PHARM BULL, V30, P1521

[32]

IMANISHI T, 1983, CHEM PHARM BULL, V31, P1191

[33]

IRIE K, 1980, NOUV J CHIM, V4, P275

[34]

IRIE K, 1981, HETEROCYCLES, V15, P201