Abstract:
:The palladium-catalyzed coupling of various 17-iodo-delta 16 steroids (17-iodo-androst-16-ene, 17-iodo-4-methyl-4-aza-androst-16-en-3-one, and 17-iodo-4-aza-androst-16-en-3-one) with dialkyl phosphites (dimethyl phosphite, diethyl phosphite, and diisopropyl phosphite) was examined in detail. The only successful condition for homogeneous coupling involved carrying out the reaction in the absence of any solvents. A large excess of dialkyl phosphite was used, which means that the phosphite itself acted as a solvent. Eight new androst-16-ene derivatives with phosphonate groups at C-17 were synthesized and characterized. These steroids are of pharmacological interest as potential 5 alpha-reductase inhibitors. Under the same conditions, methylation of lactam NH was observed using dimethyl phosphite.
journal_name
Steroidsjournal_title
Steroidsauthors
Skoda-Földes R,Kollár L,Horváth J,Tuba Zdoi
10.1016/0039-128x(95)00121-6subject
Has Abstractpub_date
1995-12-01 00:00:00pages
791-5issue
12eissn
0039-128Xissn
1878-5867pii
0039128X95001216journal_volume
60pub_type
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