STEREOCONTROLLED LINCOMYCIN SYNTHESIS

被引：32

作者：

KNAPP, S

KUKKOLA, PJ

机构：

[1] Department of Chemistry, Rutgers The State University of New Jersey, New Brunswick

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 05期

关键词：

D O I：

10.1021/jo00292a044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis from methyl a-D-galactopyranoside (6) of methyl thiolincosaminide (2), the direct synthetic precursor to lincomycin (1), is presented. The key step for controlling the off-pyranose stereocenters C-6 and C-7 is a novel intramolecular nitrogen delivery reaction using epoxy alcohol 10. Reaction of 10 with di-methylcyanamide in the presence of sodium hydride and imidazole leads to the oxazoline 14, a protected vicinal amino alcohol. The synthesis is completed by efficient exchange of acetal for thioacetal, followed by hydrolysis of the oxazoline and removal of the benzyl groups. The target 2 is obtained in 22 steps and 28% overall yield from 6. © 1990, American Chemical Society. All rights reserved.

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页码：1632 / 1636

页数：5

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