Efficient, enantioselective assembly of silanediol protease inhibitors.

ABSTRACT: A five-step assembly of silicon-protected dipeptide mimics from commercially available reagents is described. This methodology makes silanediol protease inhibitors readily available for the first time. The sequence features asymmetric hydrosilylation, a novel reduction of a silyl ether to a silyllithium reagent, and addition of this dianion to a sulfinimine, to produce the complete inhibitor skeleton with full control of stereochemistry. Oxidation of the primary alcohol to an acid completes the synthesis.

SUBMITTER: Bo Y 

PROVIDER: S-EPMC3064730 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature