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Total synthesis of the proposed structure of talarolide A

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Abstract

The proposed structure of talarolide A, a cycloheptapeptide featuring a hydroxamate moiety within the peptide backbone, was successfully synthesized. An initial attempt to synthesize a linear peptide precursor containing a C-terminal N-benzyloxy glycine residue was problematic due to an unreported on-resin reduction of N-benzyloxy glycine to glycine. After repositioning the peptide cyclization point, a new linear peptide sequence was successfully prepared using Fmoc-solid-phase peptide synthesis. Subsequent solution-phase cyclization and removal of protecting groups furnished the synthetic talarolide A in good yield. Despite the mismatch of the NMR data between the synthetic talarolide A and the natural product, a detailed structural analysis using 2D NMR spectroscopy, together with re-synthesis of the same synthetic material using two additional cyclization sites, confirmed that our synthetic product has the reported structure of talarolide A.

Graphical abstract: Total synthesis of the proposed structure of talarolide A

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Publication details

The article was received on 25 May 2018, accepted on 29 Jun 2018 and first published on 29 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB01230J
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Total synthesis of the proposed structure of talarolide A

    S. Zhang, L. M. De Leon Rodriguez, R. Huang, I. K. H. Leung, P. W. R. Harris and M. A. Brimble, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01230J

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