Denancé Mickaël, Guyot Michèle, Samadi Mohammad
Département de Chimie, LIMBP, IPEM, Université Paul Verlaine de Metz, 1 Bd Arago, Metz Technopôle, 57078 Metz, France.
Steroids. 2006 Jul;71(7):599-602. doi: 10.1016/j.steroids.2006.03.002. Epub 2006 Apr 18.
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.
首次实现了从易于获得的薯蓣皂苷元5出发，经六步合成16β-羟基-5α-胆甾烷-3,6-二酮1（一种来自海藻的代谢产物）。使用Et(3)SiH和催化量的B(C(6)F(5))(3)一步完成了三醇6伯醇的选择性脱氧，以高产率得到化合物9。用PCC氧化11，引入3,6-烯二酮官能团，进一步催化氢化和脱保护得到3,6-二酮甾体1。
