Rearrangement of the Angular Methyl Group in Dehydroabietic Acid Derivatives
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概要
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The rearrangement of the angular methyl group in dehydroabietic acid derivatives was examined. Treatment of 12-methoxy-5,8,11,13-abietatetraene (25) with boron trifluoride etherate afforded 12-methoxy-5β-methyl-10-norabieta-1(10), 8,11,13-tetraene (26). On the other hand, 12-methoxy-7-oxo-5,8,11,13-abietatetraene (27) provided three naphthalene derivatives, 28,29 and 30,on treatment with sulfuric acid in acetic anhydride. Methyl 7-oxo-5,8,11,13-abietatetraen-18-oate (5) was reduced with sodium borohydride in the presence of cerium(III) chloride heptahydrate and the resulting alcohol (32) was further treated with p-toluensulfonic acid monohydrate to give methyl 5β-methyl-10-norabieta-1(10), 6,8,11,13-pentaen-18-oate (33). On the other hand, under similar conditions, 7-oxo-5,8,11,13-abietatetraene (11) and its 12-methoxy derivative (27) were transformed into the naphthalene derivatives, 35 and 37,respectively, via the corresponding alcohols, 34 and 36.
- 社団法人日本薬学会の論文
- 1993-11-15
著者
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松本 高志
Faculty Of Integrated Arts And Sciences The University Of Tokushima
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武田 美雄
徳島大学総合科学部生物環境資源化学分野
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武田 美雄
Faculty Of Integrated Arts And Sciences The University Of Tokushima
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武田 美雄
Faculty Of Pharmaceutical Sciences The University Of Tokushima
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寺尾 博充
徳島大総合科
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寺尾 博充
Faculty of Integrated Arts and Sciences, The University of Tokushima
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和田 眞
Faculty Of Integrated Arts And Sciences University Of Tokushima
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田中 靖考
Faculty of Integrated Arts and Sciences, University of Tokushima
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田中 靖考
Faculty Of Integrated Arts And Sciences University Of Tokushima
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Takeda Yoshio
Faculty Of Integrated Arts And Science The University Of Tokushima
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Matsumoto Takashi
Faculty Of Integrated Arts And Sciences The University Of Tokushima
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