Cycloaddition of an enantiopure cyclic nitrone to maleate: Straightforward synthesis of the necine base (-)-hastanecine

被引：0

作者：

Goti, A

Fedi, V

Nannelli, L

DeSarlo, F

Brandi, A

机构：

来源：

SYNLETT | 1997年 / 05期

关键词：

pyrrolizidine alkaloids; (-)-hastanecine; necine bases; Mitsunobu reaction; enantiomerically pure cyclic nitrones;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal synthesis of the necine base (-)-hastanecine, subunit of the pyrrolizidine alkaloids hastacine and punctanecine, is reported. The key intermediate 7 is synthesized in five steps from dimesylate 11, derived from L-malic acid, in 28.3% overall yield. The correct absolute stereochemistry at C7 in the target compound is attained by means of a Mitsunobu reaction on dimesylate 11. The desired stereochemistry at the remaining stereogenic centres (C1 and C7a) derives from a highly preferential exo-anti approach in the key cycloaddition of nitrone 9 (obtained with complete regiocontrol) to dimethyl maleate.

引用

页码：577 / &

页数：4

共 25 条

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