Ring expansive routes to quinolizidine alkaloids:: Formal synthesis of (-)-lasubine II

被引：47

作者：

Gracias, V ^{[1
]}

Zeng, YB ^{[1
]}

Desai, P ^{[1
]}

Aubé, J ^{[1
]}

机构：

[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 26期

关键词：

D O I：

10.1021/ol035965c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The application of two nitrogen ring expansion reactions to lasubine alkaloid synthesis is reported. The approach involves a conjugate reduction/alkylation sequence carried out on triisopropylsilyl-protected (S)-4-(-)-hydroxycyclopentenone, the formation of the quinolizidone ring system through nitrogen ring expansion, and the addition of an arylmetallic species to the resulting lactam. This work resulted in the preparation of 2-epi-lasubine II and a formal synthesis of lasubine II.

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页码：4999 / 5001

页数：3

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