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A Reassignment of (−)-Mycothiazole and the Isolation of a Related Diol

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Rachel N. Sonnenschein,^† Tyler A. Johnson,^† Karen Tenney,^† Frederick A. Valeriote,^‡ and Phillip Crews*^†

Department of Chemistry and Biochemistry & Institute of Marine Sciences, University of California, Santa Cruz, California 95064, and Division of Hematology and Oncology, Josephine Ford Cancer Center, Detroit, Michigan 48202

J. Nat. Prod., 2006, 69 (1), pp 145–147

DOI: 10.1021/np0503597

Publication Date (Web): January 10, 2006

†

University of California, Santa Cruz.

‡

Josephine Ford Cancer Center.

To whom correspondence should be addressed. Tel: (831) 459-2603. Fax: (831) 459-2935. E-mail: phil@chemistry.ucsc.edu.

Abstract

A reinvestigation of the thiazole constituents from Cacospongia mycofijiensis, collected in Vanuatu, yielded known mycothiazole (3) plus a new derivative, mycothiazole-4,19-diol (6). The E stereochemistry at Δ^14,15 of 3 has been revised to Z and the structural features of 6 are elucidated. These compounds, which presumably arise by the action of a polyketide−nonribosomal peptide synthetase (PKS/NRPS) hybrid, possess cytotoxic properties that need further exploration.

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Published In Issue January 27, 2006
Received September 22, 2005

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A Reassignment of (−)-Mycothiazole and the Isolation of a Related Diol

Abstract

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SciFinder Links

History

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Related Content

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Natural Products as Sources of New Drugs over the Last 25 Years

A Serendipitous Discovery of Isomotuporin-Containing Sponge Populations of Theonellaswinhoei

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