Structure Revision of Similanamide to PF1171C by Total Synthesis

Journal of Natural Products
Yuichi MasudaTakayuki Doi

Abstract

The total synthesis of the proposed structure of similanamide, a cyclic hexapeptide recently isolated from the marine sponge-associated fungus Aspergillus similanensis KUFA 0013, was achieved by solid-phase synthesis of a linear precursor and solution-phase macrolactamization. The NMR spectra of our synthetic final product were not identical to those of the isolated material and led us to conclude that similanamide is identical to PF1171C, a previously reported diastereomeric hexapeptide.

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Citations

Dec 1, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xiaohan WangLigang Zhou
Jun 19, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Allan M PriorDianqing Sun
Mar 16, 2017·Natural Product Reports·John W BluntMichèle R Prinsep
Apr 7, 2020·Chemistry : a European Journal·Daniel KrahnMarkus Kaiser
Feb 16, 2021·Journal of Peptide Science : an Official Publication of the European Peptide Society·Yuka YoshidaYuichi Masuda
May 10, 2019·The Journal of Organic Chemistry·Kosuke OhsawaTakayuki Doi

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