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
收藏
页码：361 / 364
页数：4
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