Novel practical stereoselective synthesis of a bicyclic hydantoino-thiolactone as the key intermediate for production of (+)-biotin†‡ † Dedicated to esteemed Professor Li-Xin Dai on the occasion of his 100th birthday.‡ Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3ra04721k

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. 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.

SUBMITTER: Shu L 

PROVIDER: S-EPMC10475979 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature