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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

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Efficient, enantioselective assembly of silanediol protease inhibitors.

Bo Yingjian Y Singh Swapnil S Duong Hoan Quoc HQ Cao Cui C Sieburth Scott McN SM

Organic letters 20110307 7

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 ...[more]

PMID: 21381688

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