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

被引：1

作者：

Seki, Masahiko ^{[1
]}

Shimizu, Toshiaki ^{[1
]}

Inubushi, Koichi ^{[1
]}

机构：

[1] Product and Technol. Devt. Lab., Tanabe Seiyaku Co., Ltd., 3-16-89, Kashima, Yodogawa-ku, Osaka 532-8505, Japan

来源：

Synthesis | 2002年 / 03期

关键词：

Formaldehyde; -; Hydrogenation; Oxidation;

D O I：

10.1055/s-2002-20035

中图分类号：

学科分类号：

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 β-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