Abstract
Reaction of 3β-mesyloxycholestane-5α,6β-diol 6-monoacetate (1e) with potassium t-butoxide gave the 3α,5α-oxycholestan-6β-ol (4a), which rearranged further to 5β,6β-epoxycholestan-3-ol (5). Treatment of 1c with triethylamine gave cholest-2-ene-5α,6β-diol diacetate (7a), whereas heating diacetate 1c in pyridine–dimethylformamide gave cholestan-3α,5α,6β-triol 3,6-diacetate (2a). Cholest-2-ene-5α,6β-diol diacetate (7a) reacted with m-chloroperbenzoic acid to give the α-epoxide 10. Reaction of 7a with aqueous N-bromosuccinimide gave 2β-bromo-3α-hydroxy-5α,6β-diacetoxycholestane (8). Both epoxide 10 and bromohydrin 8 rearranged in acidic media to the tetrahydrofuran 11.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
14 articles.
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