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Origin of the thiopyrone CTP-431 “unexpectedly” isolated from the marine sponge Cacospongia mycofijiensis

Przeslak, Adam D.; Inman, Martyn; Lewis, William; Moody, Christopher J.

Authors

Adam D. Przeslak

Martyn Inman

William Lewis

Christopher J. Moody



Abstract

An intriguing hypothesis that latrunculin A, a well-known natural product, might have undergone transformation into the unprecedented thiopyrone CTP-431 upon long-term storage in methanol is advanced. Thus opening of the hemiacetal of latrunculin A, followed by E1CB elimination, and dehydration would give a polyene that could undergo intramolecular Diels-Alder reaction, followed by methanolysis of the thiazolidinone ring and ring closure by intramolecular thiol addition to an enone. Experimental evidence that the novel thiazolidinone to thiopyrone rearrangement can occur is presented.

The marine sponge Cacospongia mycofijiensis, found in the ocean surrounding Fiji, is a source of several polyketide natural products with interesting biological properties,1 including the tubulin binding macrolide fijianolide B (also known as laulimalide),2,3 the HIF1 signal inhibitor mycothiazole,4,5 and the macrolide latrunculins (Figure 1).6 The thiazolidinone-containing latruculins are of mixed polyketide synthesis (PKS) and non-ribosomal peptide synthesis (NRPS) origin, and latrunculin A 1 disrupts microfilament assembly to such an extent that it is the most widely used chemical tool to study actin binding.

Citation

Przeslak, A. D., Inman, M., Lewis, W., & Moody, C. J. (2018). Origin of the thiopyrone CTP-431 “unexpectedly” isolated from the marine sponge Cacospongia mycofijiensis. Journal of Organic Chemistry, 83(17), 10595-10601. https://doi.org/10.1021/acs.joc.8b01258

Journal Article Type Article
Acceptance Date Jul 25, 2018
Online Publication Date Jul 25, 2018
Publication Date Sep 7, 2018
Deposit Date Oct 1, 2018
Publicly Available Date Jul 26, 2019
Journal The Journal of Organic Chemistry
Print ISSN 0022-3263
Electronic ISSN 1520-6904
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 83
Issue 17
Pages 10595-10601
DOI https://doi.org/10.1021/acs.joc.8b01258
Public URL https://nottingham-repository.worktribe.com/output/1140750
Publisher URL https://pubs.acs.org/doi/10.1021/acs.joc.8b01258

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