Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 2, Pages 645-651Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo801993k
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Funding
- National Institutes of Health [R15 GM060967-02]
- Merck Pharmaceutical Research
- University of New Hampshire
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The application of a zinc carbenoid-mediated chain-extension reaction to a functionalized peptide isostere is reported. The cleavage site of human CVM protease was utilized as a target for testing the synthetic methodology. The utility of this chain-extension reaction is demonstrated in the preparation of an amino acid-derived alpha-unsubstituted gamma-keto ester, which is incorporated into a framework that mimics a tetrapeptide. The identification of a suitable protecting group strategy facilitated the application of a tandem reaction for the incorporation of an alpha-side chain, and the use of an oxazolidinone auxiliary provided excellent diastereocontrol in a tandem chain-extension-aldol reaction. Stereoselectivity of the tandem chain-extension-aldol reaction was determined through application of a CAN-mediated oxidative cleavage reaction.
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