Abstract
A series of C-3 oxygenated and unsubstituted (4,5)α, (4,5)β, (5,6)α, and (5,6)β epoxy steroids has been prepared, and the reactions of these compounds with strong bases (potassium tert-butoxide, LDA, and LDEA) were investigated. Only LDEA gave rise to product formation; β elimination of the epoxide to give a β-hydroxy olefin was observed in this case. The regioselectivity of product formation is consistent with a mechanism of rearrangement involving removal of a hydrogen located syn to the epoxide oxygen. In some cases, a directing influence from a polar substituent (OH) of the starting material was also apparent. The 13C nmr spectra of the steroidal epoxides used in this study were assigned; these data are diagnostic of the conformation of ring A of (4,5)α and (4,5)β epoxy steroids.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
27 articles.
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