Short synthesis of 16beta-hydroxy-5alpha-cholestane-3,6-dione a novel cytotoxic marine oxysterol |
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Authors: | Denancé Mickaël Guyot Michèle Samadi Mohammad |
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Institution: | Département de Chimie, LIMBP, IPEM, Université Paul Verlaine de Metz, 1 Bd Arago, Metz Technop?le, 57078 Metz, France. |
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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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Keywords: | Oxysterols Diosgenin Selective reduction Boron catalyst |
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