Work

Total Synthesis of Cyclosporine: Access to N-Methylated Peptides via Isonitrile Coupling Reactions

Year: 2010

Type: article

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.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja100517v

Authors: Xiangyang Wu, Jennifer L. Stockdill, Ping Wang, Samuel J. Danishefsky

Institution: Columbia University

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funder: National Cancer Institute

Awards: G1834311269, Synthesis of Antitumor Natural Products, Synthesis of Antitumor Natural Products