Short synthesis of 16beta-hydroxy-5alpha-cholestane-3,6-dione a novel cytotoxic marine oxysterol.
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.
Denancé
Mickaël
M
Département de Chimie, LIMBP, IPEM, Université Paul Verlaine de Metz, 1 Bd Arago, Metz Technopôle, 57078 Metz, France.
Guyot
Michèle
M
Samadi
Mohammad
M
D002384:Catalysis; D002778:Cholestanones / Q000138:chemical synthesis* / Q000737:chemistry; D004144:Diosgenin / Q000138:chemical synthesis / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D000461:Rhodophyta / Q000737:chemistry / Q000166:cytology
C420965:16-hydroxycholestane-3,6-dione; D002778:Cholestanones; D008387:Marine Toxins; D004144:Diosgenin