A general and efficient strategy for 7-aryloctahydroindole and cis-3a-aryloctahydroindole alkaloids: Total syntheses of (±)-γ- lycorane and (±)-crinane

Shuanhu Gao; Yong Qiang Tu; Zhenlei Song; Aixia Wang; Xiaohui Fan; Yijun Jiang

doi:10.1021/jo0507690

A general and efficient strategy for 7-aryloctahydroindole and cis-3a-aryloctahydroindole alkaloids: Total syntheses of (±)-γ- lycorane and (±)-crinane

Shuanhu Gao
, Yong Qiang Tu^*
, Zhenlei Song
, Aixia Wang
, Xiaohui Fan
, Yijun Jiang

^*Corresponding author for this work

Lanzhou University

Research output: Contribution to journal › Article › peer-review

39 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	6523-6525
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	70
Issue number	16
DOIs	https://doi.org/10.1021/jo0507690
State	Published - 5 Aug 2005
Externally published	Yes

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10.1021/jo0507690

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abstract = "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.",

author = "Shuanhu Gao and Tu, \{Yong Qiang\} and Zhenlei Song and Aixia Wang and Xiaohui Fan and Yijun Jiang",

year = "2005",

month = aug,

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volume = "70",

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T2 - Total syntheses of (±)-γ- lycorane and (±)-crinane

AU - Gao, Shuanhu

AU - Tu, Yong Qiang

AU - Song, Zhenlei

AU - Wang, Aixia

AU - Fan, Xiaohui

AU - Jiang, Yijun

PY - 2005/8/5

Y1 - 2005/8/5

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/23044462094

U2 - 10.1021/jo0507690

DO - 10.1021/jo0507690

M3 - 文章

C2 - 16050723

AN - SCOPUS:23044462094

SN - 0022-3263

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JF - Journal of Organic Chemistry

IS - 16

ER -

A general and efficient strategy for 7-aryloctahydroindole and cis-3a-aryloctahydroindole alkaloids: Total syntheses of (±)-γ- lycorane and (±)-crinane

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