Collect. Czech. Chem. Commun. 1993, 58, 2963-2976

Acrylate Side Chain Derivatives of 5β-Steroids

Vladimír Pouzar, Ivan Černý and Pavel Drašar

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


Steroids with 5β-configuration and acrylate 17β-side chain, namely (20E)-3β-hydroxy-5β-pregnane-21-carboxylate (XVI), its 3α-epimer XXVI, and homological ethyl ester XVIII were prepared from 3β-(2-tetrahydropyranyloxy)-21-norpregn-5-en-20-ol (I). The stereoselectivity of key steps was checked. Whereas hydrogenation of 4-en-3-one derivative IV gave exclusively 5β-derivative VI, the subsequent borohydride reduction yielded 3β- and 3α-hydroxy derivatives VII and XI in 1 : 4 ratio. The 3-hydroxy derivatives prepared (XVI, XVIII, and XXVI) were converted to the corresponding hemisuccinates (XX and XXVIII) and β-D-glucopyranosides (XXII, XVIV, and XXX) for latter use in biological studies.