Total synthesis of cyclosporine: Access to N-methylated peptides via lsonitrile coupling reactions Journal Article
| Authors: | Wu, X.; Stockdill, J. L.; Wang, P.; Danishefsky, S. J. |
| Article Title: | Total synthesis of cyclosporine: Access to N-methylated peptides via lsonitrile 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. Copyright © 2010 American Chemical Society. |
| Keywords: | methylation; drug structure; drug synthesis; amine; enzyme inhibitors; peptides; molecular structure; organic acids; cyclosporin a; cyclosporine; nitriles; chemical reaction; total synthesis; synthesis (chemical); isonitriles; cyclopeptide; isonitrile derivative; carboxylic acids; amide bond; thioacids; amides; amide; carboxylic acid; thioacid; cross coupling reaction; microwave radiation; couplings; ambient temperatures; coupling reaction; cyclic polypeptides; synthetic routes; tertiary amides; environmental temperature |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 132 |
| Issue: | 12 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2010-03-31 |
| Start Page: | 4098 |
| End Page: | 4100 |
| Language: | English |
| DOI: | 10.1021/ja100517v |
| PUBMED: | 20199071 |
| PROVIDER: | scopus |
| PMCID: | PMC2844917 |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 4" - "Export Date: 20 April 2011" - "CODEN: JACSA" - "Source: Scopus" |
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