Stereoselective synthesis of the antifungal antibiotic (+)-preussin

被引：33

作者：

Veeresa, G ^{[1
]}

Datta, A ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 1998年 / 54卷 / 51期

关键词：

antibiotic; chelation control; Grignard reaction; stereoselection;

D O I：

10.1016/S0040-4020(98)00981-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise total synthesis of enantiopure (+)-preussin (1) from L-phenylalanine (3) is described. The key steps involve i) syn-selective formation of the 1,2-amino alcohol fragment 2, via chelation controlled addition of allylmagnesium bromide to N-Boc-phenylalaninal, and ii) L-selectride(R) mediated stereoselective reduction of the ketone 8 to the alcohol derivative 9 with the required stereochemistry for final cyclization. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：15673 / 15678

页数：6

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