The Unexpected Isolation of CTP-431, a Novel Cytotoxic Thiopyrone from the Sponge Cacospongia mycofijiensis

Tyler A. Johnson; Taro Amagata; Allen G Oliver; Karen Tenney; Frederick A Valeriote; Phillip Crews

doi:10.1021/jo801096m

The Unexpected Isolation of CTP-431, a Novel Cytotoxic Thiopyrone from the Sponge Cacospongia mycofijiensis

Tyler A. Johnson, Taro Amagata, Allen G Oliver, Karen Tenney, Frederick A Valeriote, Phillip Crews

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Abstract

A reinvestigation of a Fijian collection of Cacospongia mycofijiensis has yielded the known mycothiazole and a novel heterocyclic, CTP-431 (1). Its structure including absolute configuration as 8R,9R,10S,13S was established using NMR data, calculated DFT 13C chemical shifts and results from X-ray crystallography. It is possible that the tricyclic skeleton of CTP-431 (1) is biosynthetically related to the macrolide latrunculin A, however the thiopyrone moiety of 1 has no previous precedent in natural products chemistry.

Original language	American English
Pages (from-to)	7255-7259
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	73
Issue number	18
DOIs	https://doi.org/10.1021/jo801096m
State	Published - 2008
Externally published	Yes

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Life Sciences

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AU - Tenney, Karen

AU - Valeriote, Frederick A

AU - Crews, Phillip

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AB - A reinvestigation of a Fijian collection of Cacospongia mycofijiensis has yielded the known mycothiazole and a novel heterocyclic, CTP-431 (1). Its structure including absolute configuration as 8R,9R,10S,13S was established using NMR data, calculated DFT 13C chemical shifts and results from X-ray crystallography. It is possible that the tricyclic skeleton of CTP-431 (1) is biosynthetically related to the macrolide latrunculin A, however the thiopyrone moiety of 1 has no previous precedent in natural products chemistry.

U2 - 10.1021/jo801096m

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