Short synthesis of 16beta-hydroxy-5alpha-cholestane-3,6-dione a novel cytotoxic marine oxysterol

Steroids
Mickaël DenancéMohammad Samadi

Abstract

The first and short synthesis of 16beta-hydroxy-5alpha-cholestane-3,6-dione 1 a metabolite from marine algae, has been achieved in six steps from readily available diosgenin 5. Selective deoxygenation of primary alcohol of triol 6 has been accomplished in one step using Et(3)SiH and catalytic amount of B(C(6)F(5))(3) to produce compound 9 in high yield. Oxidation of 11 with PCC, allowed the introduction of 3,6-ene-dione functionality, and further catalytic hydrogenation and deprotection furnished the 3,6-diketo steroid 1.

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Citations

Aug 23, 2011·Natural Product Research·Walied M AlarifSultan S Al-Lihaibi
Feb 6, 2008·Natural Product Reports·John W BluntMichèle R Prinsep
Apr 6, 2016·Journal of the American Chemical Society·Xi-Jie Dai, Chao-Jun Li
Aug 25, 2011·Plant Signaling & Behavior·Emad A Shalaby
Jun 15, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xing LiuJian-Qiang Kong
Nov 23, 2007·Natural Product Reports·James R Hanson
Jul 7, 2018·Beilstein Journal of Organic Chemistry·Anna CzarneckaPiotr Bałczewski

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