Abstract
From 17β-hydroxy-15β-[(4-methoxyphenyl)methoxy]androst-5-en-3β-yl acetate (1) by acetylation, removal of (4-methoxyphenyl)methyl group, and oxidation with Jones reagent, 15-oxoandrost-5-ene-3β,17β-diyl 3,17-diacetate (4) was prepared. (O-Carboxymethyl)hydroxylamine treatment and subsequent diazomethane methylation gave methyl ester of corresponding 15-(O-carboxymethyl)oxime derivative. Partial acid hydrolysis gave 3-acetate as a minor product, therefore the major 17-acetate was transformed in two steps into the 3-benzoate. Oxidation at position 17 and subsequent deprotection gave for both products final (15E)-3β-hydroxyandrost-5-ene-15,17-dione 15-(O-carboxymethyl)oxime (14), but for 3-acetyl derivative the whole synthesis is shorter and gave higher yield.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Collection of Czechoslovak Chemical Communications
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
