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Preparation of 6‐Methoxy Aromatic Steroids from Estradiol and by Total Synthesis
Author(s) -
Harnik M.
Publication year - 1965
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.196500046
Subject(s) - chemistry , ketone , ether , total synthesis , triol , organic chemistry , sodium hydride , diol
An easy synthesis of 6‐methoxy equilenin derivatives is described starting with 7α‐bromo‐6‐ketoestradiol 17‐acetate (Va). The resulting 6‐hydroxyequilenin dimethyl ether (VIIIa) was transformed into 17β‐acetamido‐3,6‐dimethoxy‐1,3,5(10), 6,8‐estrapentaene (IXd), the racemic form (XIIId) of which was made from the totally synthetic compounds (Xa) and (XIa), Also the D‐antipode (XXI) of 3,6‐dimethoxy‐176 ‐acetyl‐1,3,5(10), 6,8‐estrapentaene was synthesized from (VIIIa) and compared with its racemic form (XIa). Treatment of the estrapentaene (VIb) with sodium and isopropanol afforded the ketone (XVIb) which was further reduced to the triol (XVII).