Abstract:
:The synthesis of delta 7,9(11)-lanostadiene derivatives functionalized at C(32) starting from 3 beta-acetoxy-7 alpha,32-epoxylanostan-11-one has been presented. The delta 7,9(11) moiety was efficiently introduced in three steps in 71% yield by the regioselective abstraction of allylic 8 beta hydrogen. The formyl group of the key intermediate, 3 beta-benzoyloxylanosta-7,9(11)-dien-32-al, has been stereoselectively alkylated into (32S) derivative, whereas its oxidation unexpectedly afforded 3 beta-benzoyloxy-7-oxolanost-8-ene-32,11 alpha-lactone and not the corresponding acid. delta 7,9(11)-lanostadienes possessing HC(32)=O, C(32) [symbol: see text] N, HC(32S)CH3OH, H2C(32)OH, as well as some 11-keto lanostenes, were tested in vitro against several purified cholesterogenic enzymes showing moderate activity, with most the active aldehyde 16 having IC50 = 86 microM.
journal_name
Steroidsjournal_title
Steroidsauthors
Solaja BA,Dermanović M,Lim DM,Paik YK,Tinant B,Declerq JPdoi
10.1016/s0039-128x(97)00075-5subject
Has Abstractpub_date
1997-11-01 00:00:00pages
709-18issue
11eissn
0039-128Xissn
1878-5867pii
S0039128X97000755journal_volume
62pub_type
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