Expanding the limits of isonitrile-mediated amidations: On the remarkable stereosubtleties of macrolactam formation from synthetic seco -cyclosporins Journal Article
| Authors: | Wu, X.; Stockdill, J. L.; Park, P. K.; Danishefsky, S. J. |
| Article Title: | Expanding the limits of isonitrile-mediated amidations: On the remarkable stereosubtleties of macrolactam formation from synthetic seco -cyclosporins |
| Abstract: | The scope of isonitrile-mediated amide bond-forming reactions is further explored in this second-generation synthetic approach to cyclosporine (cyclosporin A). Both type I and type II amidations are utilized in this effort, allowing access to epimeric cyclosporins A and H from a single precursor by variation of the coupling reagents. This work lends deeper insight into the relative acylating ability of the formimidate carboxylate mixed anhydride (FCMA) intermediate, while shedding light on the far-reaching impact of remote stereochemical changes on the effective preorganization of seco-cyclosporins. © 2012 American Chemical Society. |
| Keywords: | molecular structure; cyclosporin a; nitriles; isonitrile derivative; stereochemistry; lactams, macrocyclic; stereoisomerism; chemical bond; amides; amide; macrocyclic lactam; acylation; coupling reagents; amidation; shedding light; bond-forming reactions; preorganization; single precursors; stereochemical changes; synthetic approach; type ii; carboxylation; cyclosporins |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 134 |
| Issue: | 4 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2012-02-01 |
| Start Page: | 2378 |
| End Page: | 2384 |
| Language: | English |
| DOI: | 10.1021/ja2103372 |
| PROVIDER: | scopus |
| PUBMED: | 22280518 |
| PMCID: | PMC3306727 |
| DOI/URL: | |
| Notes: | --- - "Export Date: 1 March 2012" - "CODEN: JACSA" - "Source: Scopus" |
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