Vinylogous Mannich reactions. Stereoselective formal synthesis of pumiliotoxin 251D

被引：57

作者：

Martin, SF ^{[1
]}

Bur, SK ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 29期

关键词：

Mannich reactions; iminium ions; asymmetric synthesis; alkaloids;

D O I：

10.1016/S0040-4020(99)00452-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of (-)-3, a known precursor of pumiliotoxin 251D, has been completed using a vinylogous Mannich reaction as a key construction. Silyloxyfuran PO added to methoxy pyrrolidine 20 in the presence of TMS-OTf to give a mixture (4.8:1) of 21 and 22 in 57% yield. Reduction and global deprotection of 21 afforded the bicyclic lactam 23. Raney Nickel mediated extrusion of the hydroxymethyl group from 23 gave (-)-3. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：8905 / 8914

页数：10

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