Clinical Analysis on Steroids. XII. Occurrence of D-Homoannulation during the Hot Acid Hydrolysis of 5β-Pregnane-3α,20α-diol Disulfate

Article abstract of DOI:10.1016/0039-128X(80)90071-9

Two D-homosteroids were isolated from the hydrolyzate of 5β-pregnane-3α,20α-diol disulfate (II) when it was refluxed in 3N hydrochloric acid.The structures of these steroids have been elucidated as 17α-methyl-D-homo-5β-androstane-3α,17aβ-diol (VI) and 17α-methyl-17aβ-chloro-D-homo-5β-androstan-3α-ol (VIII) by instrumental analyses.The former was identical with a synthetic specimen derived from 5β-pregnane-3α,20β-diol disulfate (IV) by uranediol rearrangement.The main hydrolyzates obtained were 17α-ethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol (V) and 5β-pregnane-3α-20α-diol (III).