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

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Boland,  Sebastian
Max Planck Institute of Molecular Cell Biology and Genetics, Max Planck Society;

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Kurzchalia,  Teymuras V.
Max Planck Institute of Molecular Cell Biology and Genetics, Max Planck Society;

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Citation

Saini, R., Boland, S., Kataeva, O., Schmidt, A. W., Kurzchalia, T. V., & Knölker, H.-J. (2012). Stereoselective synthesis and hormonal activity of novel dafachronic acids and naturally occurring steroids isolated from corals. Organic & Biomolecular Chemistry, 10(21), 4159-4163.


Cite as: https://hdl.handle.net/21.11116/0000-0001-08B3-C
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.