Stereocontrolled total synthesis of alkaloid G via the oxy-anion cope rearrangement and improved total synthesis of (+)-ajmaline

被引：40

作者：

Wang, T ^{[1
]}

Xu, QG ^{[1
]}

Yu, P ^{[1
]}

Liu, XX ^{[1
]}

Cook, JM ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Milwaukee, WI 53201 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 03期

关键词：

D O I：

10.1021/ol000331g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The oxy-anion Cope rearrangement followed by protonation of the enolate which resulted under conditions of kinetic control has been employed to generate the key asymmetric centers at C(15), C(16), and C(20) in alkaloid G (1) and (+)-ajmaline (2) in a highly stereocontrolled fashion. The aldehyde 7b from this process has been converted into alkaloid G (1) and (+)ajmaline (2) in 36% and 13% overall yields (11 reaction vessels from 3), respectively.

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页码：345 / 348

页数：4

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