A Conversion of 4α-Bromoshionan-3-one into D : B-Friedobacchara-1,5(10)-dien-3-one and A Preparation of D : B-Friedo-bacchar-5(10)-en-3-one

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Abstract
A mixture of D : B-friedo-bacchar-5(10)-en-3-one (2) and D : B-friedo-bacchar-5-en-3-one (4), prepared from 4α-bromoshionan-3-one (3) by the known procedures, was converted into a mixture of 2ξ-bromo-D : B-friedobacchar-5(10)-en-3-one (6) and 2ξ-bromo-D : B-friedo-bacchar-5-en-3-one (7) by bromination with pyridinium tribromide. The mixture (6 and 7) was subjected to dehydrobromination to give D : B-friedo-bacchara-1,5(10)-dien-3-one (5). Hydrogenation of the dienone (5) gave D : B-friedo-bacchar-5(10)-en-3-one (2).