An efficient, stereoselective synthesis of (-)-bulgecinine from (S)-aspartic acid

被引：14

作者：

Fehn, S ^{[1
]}

Burger, K ^{[1
]}

机构：

[1] UNIV LEIPZIG,DEPT ORGAN CHEM,D-04103 LEIPZIG,GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(97)00215-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A stereoselective synthesis of (2S,4S,5R)4-hydroxy-5-hydroxymethylproline 1 starting from (S)-aspartic acid 2 is described. The key step of the synthesis is the [Rh(OAc)(2)](2) catalyzed stereospecific transformation (de > 98%) of the hexafluoroacetone protected diazoketone 5 into the 4-oxoproline derivative 7. The keto function of 7 was reduced with high diastereoselectivity (de > 88%) to give the 4-cis-hydroxyproline derivative 8. After deprotection (-)-bulgecinine 1 was obtained from 9 on reduction of the ester moiety with LiBHEt3. (C) 1997 Elsevier Science Ltd.

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页码：2001 / 2005

页数：5

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