文献类型：期刊文献

英文题名：Novel practical stereoselective synthesis of a bicyclic hydantoino-thiolactone as the key intermediate for production of (+)-biotin

作者：Shu, Lei[1];Yang, Zhi-Wei[1];Cao, Ren-Xu[1];Qiu, Xiao-Xia[1];Ni, Feng[2];Shi, Xiao-Xin[1]

机构：[1]East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Sch Pharm, Minist Educ, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[2]Shanghai Shyndec Pharmaceut Co Ltd, 378 Jian Lu Rd, Shanghai, Peoples R China

年份：2023

卷号：13

期号：37

起止页码：26160

外文期刊名：RSC ADVANCES

收录：;EI(收录号：20233814742120);WOS:【SCI-EXPANDED(收录号:WOS:001057685600001)】；

基金：We are grateful to the National Natural Science Foundation of China (No. 20972048, 20172015) for the financial support of this work.

语种：英文

外文关键词：Catalysis - Coenzymes - Isomerization - Stereoselectivity

摘要：Bicyclic hydantoinothiolactone (1), as the key intermediate for production of (+)-biotin, has been efficiently and high-stereoselectively synthesized from the cheap starting material l-cystine via nine steps in 44% overall yield. In this new practical synthesis, there are two characteristic steps worthy of note. One step is TMSOTf-catalyzed efficient cyanation of (3S,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-1H,3H-imidazo[1,5-c]thiazol-7-yl acetate, the other step is DBU-catalyzed rapid isomerization of trans-isomer to cis-isomer of the bicyclic hydantoinothiolactone. Bicyclic hydantoinothiolactone, as the key intermediate for production of (+)-biotin, has been efficiently and high-stereoselectively synthesized from the cheap starting material l-cystine via nine steps in 44% overall yield.