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Studies in Syntheses of Steroid Metabolites. I.
Author(s) -
Harnik M.
Publication year - 1963
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.196300032
Subject(s) - chemistry , androstane , solvolysis , sodium borohydride , steroid , olefin fiber , sodium , stereochemistry , organic chemistry , combinatorial chemistry , biochemistry , hydrolysis , hormone , catalysis
Several approaches to the synthesis of 3α, 11β‐dihydroxy‐5α‐androstane‐17‐one (Vila) and 3α‐hydroxy‐5α‐androstane‐11,17‐dione (XIIa) are discussed. The preferred route involves selective sodium borohydride reduction of 5α‐androstane‐3,11,17‐trione (V) to 3β‐hydroxy‐5α‐androstane‐11,17‐dione (VIa) and solvolysis of its tosylate (VIc) to afford a mixture of the ketoalcohol (XIIa) and the olefin (VIIIb). The latter is then converted, through the ketals (XIb) and (XIIIb), into the diolone (VIIa).