Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Diterpenoids. XXXVIII. Conversion of l-Abietic Acid into Steroidal Skeletons : Formation of the D-Ring (1)
田原 昭嶋垣 正之伊藤 正善針谷 義弘恩田 政行
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1975 年 23 巻 12 号 p. 3189-3202

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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 (ONO2)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. RuO2 reduction of 6 and successive Pb (OAc)4 oxidation to 17 is also described.
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© The Pharmaceutical Society of Japan
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