Divergent solid-phase synthesis of natural product-inspired bipartite cyclodepsipeptides : total synthesis of seragamide A

H.-D. Arndt, S. Rizzo, Chr. Nöcker, V.N. Wackchaure, L.G. Milroy, V. Bieker, A. Calderon, T.T.N. Tran, S. Brand, L. Dehmelt, H. Waldmann

Research output: Contribution to journalArticleAcademicpeer-review

14 Citations (Scopus)

Abstract

Macrocyclic natural products (NPs) and analogues thereof often show high affinity, selectivity, and metabolic stability, and methods for the synthesis of NP-like macrocycle collections are of major current interest. We report an efficient solid-phase/cyclorelease method for the synthesis of a collection of macrocyclic depsipeptides with bipartite peptide/polyketide structure inspired by the very potent F-actin stabilizing depsipeptides of the jasplakinolide/geodiamolide class. The method includes the assembly of an acyclic precursor chain on a polymeric carrier, terminated by olefins that constitute complementary fragments of the polyketide section and cyclization by means of a relay-ring-closing metathesis (RRCM). The method was validated in the first total synthesis of the actin-stabilizing cyclodepsipeptide seragamide A and the synthesis of a collection of structurally diverse bipartite depsipeptides.
Original languageEnglish
Pages (from-to)5311-5316
Number of pages6
JournalChemistry : A European Journal
Volume21
Issue number14
DOIs
Publication statusPublished - 2015

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