Journal
ORGANIC LETTERS
Volume 13, Issue 7, Pages 1787-1789Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol2002978
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Funding
- National Institutes of Health [R01GM076471]
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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.
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