A novel synthesis of a key intermediate for (+)-biotin from L-aspartic acid

被引：0

作者：

Seki, M ^{[1
]}

Shimizu, T ^{[1
]}

Inubushi, K ^{[1
]}

机构：

[1] Tanabe Seiyaku Co Ltd, Prod & Technol Dev Lab, Yodogawa Ku, Osaka 5328502, Japan

来源：

SYNTHESIS-STUTTGART | 2002年 / 03期

关键词：

vitamins; stereoselective synthesis; amino acids; aldol reaction; rearrangement;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aldol reaction of an N-Cbz-3-amino-4-butanolide 4, derived from L-aspartic acid, with formaldehyde gave the trans-disubstituted 3-amino-4-butanolide 5 stereoselectively. Following protection of the hydroxyl group of 5, amidation and oxidation provided the beta-substituted L-asparagine derivative 6. The Hofmann rearrangement of 6 with sodium hypochlorite in the presence of sodium hydroxide and subsequent hydrogenation gave the bicyclic lactone 11, which upon dibenzylation and thionation, gave the thiolactone 2, a key intermediate for the synthesis of (+)-biotin (1).

引用

页码：361 / 364

页数：4

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