| Abstract: | Selective ring opening of the cyclopropyl moiety of binor-S was accomplished by several methods including acidic hydrolysis, bromination, and bydrobromination. The crystal structure of dibromide adduct 3 was solved by X-ray diffraction analysis. Debrominations of 3 yielded either 1 or 4a , whereas dehydrobromination yielded a 3-substituted monobromide 6a . The mechanism of conversion of 3 to 6a is depicted as involving intermediate 7 ; the existence of 7 is supported by the isolation of olefin 8 . Oxidation of alcohol 4c produced ketone 11a which was either oxidized to lactone 12 or transformed to a methylene derivative 11b . Hydroboration of 11b followed by quenching with hydrogen peroxide produced a hydroxymethyl derivative 14 . |
