Issue 37, 2023

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
14 7月 2023
Accepted
09 8月 2023
First published
04 9月 2023
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2023,13, 26160-26168

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

L. Shu, Z. Yang, R. Cao, X. Qiu, F. Ni and X. Shi, RSC Adv., 2023, 13, 26160 DOI: 10.1039/D3RA04721K

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