A General and Efficient Strategy for 7-Aryloctahydroindole and cis-3a-Aryloctahydroindole Alkaloids:  Total Syntheses of (±)-γ-Lycorane and (±)-Crinane

A general and efficient approach to both 7-aryloctahydroindole and cis-3a-aryloctahydroindole alkaloids has been developed. The key step involves Michael additions of the corresponding kinetics and thermodynamics lithium enolates of ketone 9 to the versatile building blocks:  nitroethylene 10. Two r...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-08, Vol.70 (16), p.6523-6525
Main Authors: Gao, Shuanhu, Tu, Yong Qiang, Song, Zhenlei, Wang, Aixia, Fan, Xiaohui, Jiang, Yijun
Format: Article
Language:English
Subjects:
Amaryllidaceae Alkaloids - chemical synthesis
Amaryllidaceae Alkaloids - chemistry
Biological Factors - chemical synthesis
Biological Factors - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indoles - chemical synthesis
Indoles - chemistry
Kinetics
Lithium - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Thermodynamics
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Summary:A general and efficient approach to both 7-aryloctahydroindole and cis-3a-aryloctahydroindole alkaloids has been developed. The key step involves Michael additions of the corresponding kinetics and thermodynamics lithium enolates of ketone 9 to the versatile building blocks:  nitroethylene 10. Two representative members, (±)-γ-lycorane and (±)-crinane, have been synthesized in 22 and 36% overall yields, respectively.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0507690