Stereochemistry of Steroid containing Aromatic A-Ring. I. Reaction of 9 (11)-Dehydroestrone.

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Bromination of 3-methoxy-9 (11)-dehydroestrone (II) gave equilenin methylether (IV). Hydroxybromination of 3-acetoxy-9 (11)-dehydrostrone (III) with N-bromosuccinimide in the presence of perchloric acid afforded a bromohydrin (VI), whose structure was assigned 3, 9α-dihydroxy-11β-bromoestra-1, 3, 5 (10)-trien-17-one 3-acetate, on the basis of the resistance of hydroxyl group to acetylation and oxidation, and by leading to 9α, 11α-epoxide (VII) and triol (IX).

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