Stereoselective total synthesis of (±)-swainsonine based on endo mode cyclization

被引：58

作者：

Mukai, C ^{[1
]}

Sugimoto, Y ^{[1
]}

Miyazawa, K ^{[1
]}

Yamaguchi, S ^{[1
]}

Hanaoka, M ^{[1
]}

机构：

[1] Kanazawa Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 920, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 18期

关键词：

D O I：

10.1021/jo980598h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new stereoselective total synthesis of (+/-)-swainsonine is described. Successive treatment of cis-3,4-epoxy- 7-(p-toluene sulfonamido)-1-heptyne with dicobalt octacarbonyl, Lewis acid, and cerium(IV) ammonium nitrate effected stereoselective formation of the trans-2-ethynyl-3-hydroxypiperidine skeleton with retention of configuration at the propynyl center. The piperidine derivative thus prepared was converted into the title compound efficiently.

引用

页码：6281 / 6287

页数：7

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