Abstract:
On exposure to the potential carcinogen 1,3-butadiene, the major
urinary metabolite in humans is N-acetyl-S-(3,4-dihydroxybutyl)cysteine. A
novel, stereoselective synthesis of this cysteine–butadiene metabolite has been
developed that is suitable for the production of either diastereomer for use in
occupational exposure analysis. L-Cysteine and 4-bromo-1-butene are coupled
via an SN2 reaction to give the core structure. A Sharpless asymmetric dihydroxylation
using the dihydroquinidine (DHQD) ligand provided the terminal 1,2-diol
with the 3-hydroxyl group in the R configuration.
Supplementary materials are available for this article. Go to the publisher’s online
edition of Synthetic Communications1 to view the free supplemental resource
