4.6 Article

Stereoselective synthesis and hormonal activity of novel dafachronic acids and naturally occurring steroids isolated from corals

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 21, Pages 4159-4163

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob25394a

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Funding

  1. ESF EuroMembrane Network (DFG) [KN 240/13-1]
  2. Deutsche Forschungsgemeinschaft [KN 240/16-1]

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A stereoselective synthesis of (25S)-Delta(1)-, (25S)-Delta(1,4)-, (25S)-Delta(1,7)-, (25S)-Delta(8(14))-, (25S)-Delta(4,6,8(14))-dafachronic acid, methyl (25S)-Delta(1,4)-dafachronate and (25S)-5 alpha-hydroxy-3,6-dioxocholest-7-en-26-oic acid is described. (25S)-Delta(1,4)-Dafachronic acid and its methyl ester are natural products isolated from corals and have been obtained by synthesis for the first time. (25S)-5 alpha-Hydroxy-3,6-dioxocholest-7-en-26-oic acid represents a promising synthetic precursor for cytotoxic marine steroids.

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