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Total synthesis of cyclosporine: access to N-methylated peptides via isonitrile coupling reactions.

ABSTRACT: Recent developments in the use of isonitriles to furnish secondary and tertiary amide bond formations have been applied to a novel total synthesis of the important cyclic polypeptide cyclosporine A. Specifically, the disclosed synthetic route demonstrates the utility of microwave-mediated carboxylic acid isonitrile couplings, thioacid isonitrile couplings at ambient temperature, and isonitrile-mediated couplings of carboxylic acids and thioacids with amines to form challenging amide bonds.

SUBMITTER: Wu X

PROVIDER: S-EPMC2844917 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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Total synthesis of cyclosporine: access to N-methylated peptides via isonitrile coupling reactions.

Wu Xiangyang X Stockdill Jennifer L JL Wang Ping P Danishefsky Samuel J SJ

Journal of the American Chemical Society 20100301 12

Recent developments in the use of isonitriles to furnish secondary and tertiary amide bond formations have been applied to a novel total synthesis of the important cyclic polypeptide cyclosporine A. Specifically, the disclosed synthetic route demonstrates the utility of microwave-mediated carboxylic acid isonitrile couplings, thioacid isonitrile couplings at ambient temperature, and isonitrile-mediated couplings of carboxylic acids and thioacids with amines to form challenging amide bonds. ...[more]

PMID: 20199071

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