Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
The Bromination of 13α-Androstan-15-one
南原 利夫細野 宏碓氷 昌宏呉 励然
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1971 年 19 巻 12 号 p. 2555-2560

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In order to examine the behaviors toward bromination 3β-acetoxy-5α, 13α-androstan-15-one (X) was prepared from the 17-keto steroid (I) according to the method worked out by Djerassi, et al. with the C/D-trans steroid (see Chart 1). On treatment with bromine in acetic acid in the presence of hydrogen bromide, bromination occurred exclusively at C-16 yielding a mixture of 16β-bromo and 16, 16-dibromo derivatives (XI and XII), which could be separated readily by preparative thin-layer chromatography.
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© The Pharmaceutical Society of Japan
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