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Stereoselective formation and bf3-catalysed cleavage of steroidal α-epoxyketones

✍ Scribed by J.R. Bull

Publisher
Elsevier Science
Year
1968
Tongue
French
Weight
166 KB
Volume
9
Category
Article
ISSN
0040-4039

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✦ Synopsis

The base-catalpaed epoxidation of a,S-unsaturated ketones often proceeds with a high degree of stereoeelectivity (1). Although a variety of eteroidal u-epoxyketones has been prepared in this way (2). the reaction6 of A&4-and A4-6-ketones with alkaline hydrogen peroxide have not been reported.

Choleet-S-en-4-one (I) in methanol at 2C" reacted with a slight excess of aqueous 4N potassirnn hydroxide aud 100 vol. hydrogen peroxide to give after 40 hr.. a 70x

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In Part I the reaction8 of HP with ateroldal a,p-epoxyketones were shown to occur reglospeoifically by two alternative modes, B or a\*, depending upon the eolvent employed.3 In neat CHC13, two model compound8 48,5aepoxy-178~hydroxy-endrosten-3-one lb end 4r,5a-epoxy-178-hydroxy-androeten-