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Org Biomol Chem. 2012 Jun 7;10(21):4159-63. doi: 10.1039/c2ob25394a. Epub 2012 Mar 21.

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

Author information

1
Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.

Abstract

A stereoselective synthesis of (25S)-Δ(1)-, (25S)-Δ(1,4)-, (25S)-Δ(1,7)-, (25S)-Δ(8(14))-, (25S)-Δ(4,6,8(14))-dafachronic acid, methyl (25S)-Δ(1,4)-dafachronate and (25S)-5α-hydroxy-3,6-dioxocholest-7-en-26-oic acid is described. (25S)-Δ(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)-5α-Hydroxy-3,6-dioxocholest-7-en-26-oic acid represents a promising synthetic precursor for cytotoxic marine steroids.

PMID:
22434373
DOI:
10.1039/c2ob25394a
[Indexed for MEDLINE]

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