Stereoselective approach to hydroxyindolizidines: Protection/deprotection of the nitrone functionality via cycloaddition/retrocycloaddition

被引：38

作者：

Cordero, FM ^{[1
]}

Gensini, M ^{[1
]}

Goti, A ^{[1
]}

Brandi, A ^{[1
]}

机构：

[1] Univ Florence, CNR, Dipartimento Chim Organ U Schiff, Ctr Studio Chim Struttura Composti Eterociclici, I-50121 Florence, Italy

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 16期

关键词：

D O I：

10.1021/ol006125q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The enantiomerically pure Indolizidine (-)-21 has been synthesized starting from L-malic acid. The key intermediate 20 has been assembled through an intramolecular 1,3-dipolar cycloaddition of a nitrone generated in situ by retrocycloaddition from isoxazolidine 17 or 18. The configuration of the new three stereocenters was set up with complete control in the cycloaddition step, The presented synthetic route provides a general and highly selective methodology toward indolizidines having the [1,8a]-cis configuration.

引用

页码：2475 / 2477

页数：3

共 36 条

[1]

[Anonymous], 1 3 DIPOLAR CYCLOADD

[2] A NITRONE-BASED APPROACH TO THE ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-ANISOMYCIN [J].