Total Synthesis of Keramamides A and L from a Common Precursor by Late-Stage Indole Synthesis and Configurational Revision

Angewandte Chemie
Lukas Junk, Uli Kazmaier

Abstract

The marine natural products keramamide A and L, members of the class of anabaenopeptin-type peptides, were synthesized for the first time by a convergent and flexible route. The installation of the substituted tryptophan moieties was accomplished at the very end of the synthesis on the cyclic peptides, and thus enabled the synthesis of both natural products from one common precursor. The preparation of several epimers clearly indicates that the originally proposed relative configurations of both Keramamides A and L were not correct.

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Citations

Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Oct 23, 2020·Chemistry : a European Journal·Oliver Andler, Uli Kazmaier
May 1, 2021·International Journal of Molecular Sciences·Jia-Nan ZhangHong-Jie Zhang
May 18, 2021·Organic & Biomolecular Chemistry·Oliver Andler, Uli Kazmaier
Jul 17, 2021·Organic Letters·Michael Kohr, Uli Kazmaier
Feb 13, 2019·The Journal of Organic Chemistry·Lukas Junk, Uli Kazmaier

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