The synthesis of Delta(7,9(11))-lanostadiene derivatives functionalize
d at C(32) starting from 3 beta-acetoxy-7 alpha,32-epoxylanostan-11-on
e has been presented. The Delta(7,9(11)) moiety was efficiently introd
uced in three steps in 71% yield by the regioselective abstraction of
allylic 8 beta hydrogen. The formyl group of the key intermediate, 3 b
eta-benzoyloxylanosta-7,9(11)-dien-32-al, has been stereoselectively a
lkylated into (32S) derivative, whereas its oxidation unexpectedly aff
orded 3 beta-benxoyloxy-7-oxolanost-8-ene-32,11 alpha-lactone and not
the corresponding acid. Delta(7,9(11))-lanostadienes possessing HC(32)
=O, C(32)=N, HC(32S)CH3OH, H2C(32)OH, as well as some 11-keto lanosten
es, were tested in vitro against several purified cholesterogenic enzy
mes showing moderate activity, with most the active aldehyde 16 having
IC50 = 86 mu M. (C) 1997 by Elsevier Science, Inc.