DE NOVO ASYMMETRIC APPROACH TO 8a-epi-SWAINSONINE

被引：15

作者：

Coral, Jason A. ^{[1
]}

Guo, Haibing ^{[1
]}

Shan, Mingde ^{[1
]}

O'Doherty, George A. ^{[1
]}

机构：

[1] W Virginia Univ, Dept Chem, Morgantown, WV 26506 USA

来源：

HETEROCYCLES | 2009年 / 79卷

基金：

美国国家科学基金会;

关键词：

De Novo Asymmetric Synthesis; Noyori Reduction; Acylfuran; Swainsonine; 8a-epi-Swainsonine;

D O I：

10.3987/COM-08-S(D)12

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved method for the synthesis of (-)-8a-epi-swainsonine has been developed with 9 fewer steps than the original route. The synthetic improvements include a two-step procedure for the preparation of benzyl 4-(furan-2-yl)-4-oxobutylcarbamate from pyrrolidin-2-one and a two-step procedure for the preparation of benzyl 3-((3aS,4S,6R,7aR)-4-(benzyloxy)tetrahydro-2,2-dimethyl-7-oxo-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)- propylcarbamate from benzyl 3-((2R,6S)-6-(benzyloxy)-3,6-dihydro-3-oxo-2H-pyran-2yl)propylcarbamate.

引用

页码：521 / 529

页数：9