De novo asymmetric synthesis of 8a-epi-swainsonine

被引：56

作者：

Abrams, Jason N. ^{[1
]}

Babu, Ravula Satheesh ^{[1
]}

Guo, Haibing ^{[1
]}

Le, Dianna ^{[1
]}

Le, Jennifer ^{[1
]}

Osbourn, Joshua M. ^{[1
]}

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

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 05期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/jo702476q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An enantioselective and diastereocontrolled approach to 8a-epi-D-swainsonine has been developed from achiral furfural. The key step to this synthesis was a one-pot procedure for the hydrogenolytic removal of two protecting groups and two intramolecular reductive amination reactions. The absolute stereochemistry was introduced by asymmetric Noyori reduction of furfuryl ketone. This route relies on diastereoselective palladium-catalyzed glycosylation to install the anomeric bond, and Luche reduction, diastereoselective dihydroxylation to set up the manno-stereochemistry of the indolizidine precursor.

引用

页码：1935 / 1940

页数：6

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