Steroid Series. XXIV. Photolysis of 3α, 5-Cyclo-6-oxo-17β-acetoxy-5α-androstan-19-oic Acid and 6-Oxo-17β-acetoxy-5α-androstan-19-oic Acid

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概要

• 論文の詳細を見る

• Irradiation of 3α, 5-cyclo-6-oxo-17β-acetoxy-5α-androstan-19-oic acid (1) in tertiary butyl alcohol yielded 4α-tert-butoxy-6,6-dihydroxy-17β-acetoxy-5α-androstan-19-oic acid 6,19-lactone (2) and 6-oxo-17β-acetoxyandrost-4-en-19-oic acid (3) in 50% and about 10% yields respectively. The former (2) was found to be formed by photochemical addition of tertiary butyl alcohol to the α, β-unsaturated ketone system in the latter (3). In connection with the mechanism of the above reaction, photolysis of 6-oxo-17β-acetoxy-5α-androstan-19-oic acid (9) in methanol and tertiary butyl alcohol is conducted to yield 5,6-secocarboxylic acid derivatives (17,19,20,21), and irradiation of methyl 3α, 5-cyclo-6-oxo-17β-acetoxy-5α-androstan-19-oate in tertiary butyl alcohol was also described yielding methyl 4α-tert-butoxy-6-oxo-17β-acetoxy-5α-androstan-19-oate (4) and methyl 6-oxo-17β-acetoxyandrost-4-en-19-oate (14).

• 公益社団法人日本薬学会の論文
• 1971-04-25

著者

• 小島 孝一

  Central Research Laboratories, Sankyo Co., Ltd.

• 小島 孝一

  Medicinal Chemistry Research Laboratories Sankyo Co. Ltd.

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