Abstract:
:We report the synthesis of 3 beta,15 beta,17 alpha-trihydroxy-5-pregnen-20- one (1) from 3 beta,15 beta-dihydroxy-5,16-pregnadien-20-one (11) in 7 steps using boronate derivatives as a means of protecting the 17,20-glycol side-chain of steroid intermediates. 16 alpha,17 alpha-Epoxy-3 beta,15 beta-dihydroxy-5- pregnen-20-one (12), an intermediate in the synthesis was prepared by epoxidation of 11 using a mixture of sodium hydroxide and hydrogen peroxide. Reduction of 12 with lithium aluminium hydride gave the two isomers of 5-pregnene-3 beta, 15 beta,17 alpha,20 (S+R)-tetrol (13a and 13b) which on subsequent reaction with n-butyl boronic acid gave 5-pregnene-3 beta,15 beta,17 alpha, 20(S+R)-tetrol 17 alpha,20-butyl boronate (15a and 15b). Acetylation with acetic anhydride and pyridine yielded 3 beta,15 beta-diacetoxy-5-pregnene-17 alpha,20(S+R)-diol 17 alpha,20(S+R)-butyl boronate (15c and 15d). Oxidative cleavage of the boronic ester using sodium hydroxide and hydrogen peroxide gave 3 beta,15 beta-diacetoxy-5-pregnene-17 alpha,20(S+R)-diol (13c and 13d). After isolation of these latter two products, dibromide protection of the C-5,6 olefin of 13d and oxidation with N-bromosuccinimide gave 3 beta,15 beta-diacetoxy-17 alpha-hydroxy-5-pregnen-20-one (16) which on deacetylation gave in good yield (35%) the desired product 3 beta,15 beta,17 alpha-trihydroxy-5-pregnen-20-one (1) in an overall yield of 24% from 11.
journal_name
Steroidsjournal_title
Steroidsauthors
Joannou GE,Reeder AYdoi
10.1016/0039-128x(95)00169-qsubject
Has Abstractpub_date
1996-01-01 00:00:00pages
11-7issue
1eissn
0039-128Xissn
1878-5867pii
0039128X9500169Qjournal_volume
61pub_type
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