Total synthesis of the cyclic dodecapeptides wewakazole and wewakazole B

Inman, Martyn; Dexter, Hannah L.; Moody, Christopher J.

Abstract

The cyclic dodecapeptides wewakazole and wewakazole B have been synthesized by a divergent strategy via a common tris-proline containing oxazole octapeptide and two separate bisoxazole containing tetrapeptide units, followed by peptide coupling and macrocyclization. The three oxazole amino acid fragments are readily accessible by rhodium(II)-catalysed amide N–H insertion of diazocarbonyl compounds, or by the cycloaddition of rhodium carbenoids with nitriles.

Citation

Inman, M., Dexter, H. L., & Moody, C. J. (2017). Total synthesis of the cyclic dodecapeptides wewakazole and wewakazole B. Organic Letters, 19(13), 3454-3457. https://doi.org/10.1021/acs.orglett.7b01393

• Journal Article Type: Article
• Acceptance Date: Jun 6, 2017
• Online Publication Date: Jun 15, 2017
• Publication Date: Jul 7, 2017
• Deposit Date: Jul 11, 2017
• Publicly Available Date: Jul 11, 2017
• Journal: Organic Letters
• Print ISSN: 1523-7060
• Electronic ISSN: 1523-7052
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 19
• Issue: 13
• Pages: 3454-3457
• DOI: https://doi.org/10.1021/acs.orglett.7b01393
• Public URL: https://nottingham-repository.worktribe.com/output/865884
• Publisher URL: http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b01393
• Contract Date: Jul 11, 2017