Collect. Czech. Chem. Commun. 2000, 65, 1156-1162

Allopregnanolone Derivatives: Synthesis of 3α-Hydroxy-7a-homo-5α-pregnan-20-one

Hana Chodounská* and Alexander Kasal

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


3α-Hydroxy-7a-homo-5α-pregnan-20-one and 3α-hydroxy-7a-homo-5α-pregnane-7,20-dione were prepared from (20R)-3α-(methoxymethoxy)-7-oxo-5α-pregnan-20-yl benzoate. Homo- logation of the B ring was carried out by the Demyanov rearrangement of the corresponding cyanohydrin. Alkaline hydrolysis of the protecting group and oxidation of the formed 20-hydroxy group and deprotection of the 3-hydroxy group were performed either with (20R)-3α-(methoxymethoxy)-7-oxo-7a-homo-5α-pregnan-20-ol derivative or with the product of the Huang Minlon deoxygenation at carbon 7.

Keywords: Steroids; Epalons; Allopregnanolone; GABAA-Modulators; 3α,5α-Tetrahydroprogesterone; Huang Minlon reduction.

References: 14 live references.