The unexpected isolation of CTP-431, a novel thiopyrone from the sponge Cacospongia mycofijiensis

J Org Chem. 2008 Sep 19;73(18):7255-9. doi: 10.1021/jo801096m. Epub 2008 Aug 21.

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 (13)C 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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards
  • Models, Chemical
  • Models, Molecular
  • Molecular Conformation
  • Porifera / chemistry*
  • Pyrones / chemistry
  • Pyrones / isolation & purification*
  • Reference Standards

Substances

  • CTP-431
  • Pyrones