Diterpenoids. XXXVIII. Conversion of l-Abietic Acid into Steroidal Skeletons : Formation of the D-Ring (1)
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概要
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The steroidal D-rings (31 and 37), along with 32 and 38,were synthesized by the use of a part or whole of the carbon units of the isopropyl group of l-abietic acid (1), via oxidation of 18 or 20 with Tl (ONO_2)_3,or addition reaction of 20 with 1,1-dichloroethylene, and modifications of the functionality, followed by Friedel-Crafts cyclization. Cyclization to the 14-position (formation of 31 or 37) in 30 or 35 was always predominant over that to the 12-position (formation of 32 or 38). In attempts for functionalization of the isopropyl group with Pb (OAc)_4,9,a hopeful intermediate to syntheseze quinoid diterpenes, was obtained via 3,4,5 and 6. RuO_2 reduction of 6 and successive Pb (OAc)_4 oxidation to 17 is also described.
- 1975-12-25
著者
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恩田 政行
School of Pharmaceutical Sciences, Kitasato University
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恩田 政行
Shenyang Pharmaceutical University
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針谷 義弘
北里大薬
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田原 昭
Rikagaku Kenkyusho (The Institute of Physical and Chemical Research)
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嶋垣 正之
理研
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嶋垣 正之
Rikagaku Kenkyusho (The Institute of Physical and Chemical Research)
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