Synthesis of Pygmaeocine E, a Linear Abietane Diterpene from Pygmaeopremna herbacea (ROXB.) MOLDENKE

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概要

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• Methyl 12-methoxy-7-oxo-8,11,13-abietatrien-18-oate (10), prepared from (+)-dehydroabietic acid (9), was rearranged into methyl 7-isopropyl-6-methoxy-1,10-dimethyl-1,2,3,4-tetrahydroanthracene-1-carboxylate (13) via a series of reaction : dehydrogenation with selenium(IV) oxide, sodium borohydrie reduction, and dehydration with boron trifluoride etherate. Reduction of 13 with lithium aluminum hydride afforded an alcohol (14), which was further reaffanged into 2-isopropyl-3-methoxy-5,9-dimethyl-7,8-dihydro-6H-cyclohepta[b]naphthalene (16) by treatment with methanesulfonyl chloride in pyridine. The alcohol 14 was then converted into 7-isopropyl-5,6-dimethoxy-1,1,10-trimethyl-1,2,3,4-tetrahydroanthracene (22) by means of the following reaction : pyridinium chlorochromate oxidation, Huang-Minlon reduction, demethylation, oxidation with Fremy's salt, catalytic hydrogenation, and methylation. Compound 22 was also prepared from methyl 11,12-dimethoxy-7-oxo-8,11,13-abietatrien-18-oate (23) via methyl 7-isopropyl-5,6-dimethoxy-1,10-dimethyl-1,2,3,4-tetrahydroanthracene-1-carboxylate (26). Treatment of 22 with DDQ produced an enone (29), which was converted into a diosphenol derivative (31) via a series of reaction : catalytic hydrogenation, and oxidations with Jones reagent and then with oxygen in the presence of potassium tert-butoxide. Demethylation of 31 with ethanethiol and anhydrous aluminum chloride afforded pygmaeocine E (1) and 3,6-dihydroxy-7-isopropyl-1,1,10-trimethyl-1,2-dihydroanthracen-2-one (32).

• 社団法人日本薬学会の論文
• 1996-07-15

著者

• 高石 喜久

  徳島大院薬

• Takeda Yoshio

  Faculty of Pharmacy, Yasuda Womens University

• Takeda Y

  Fac. Of Integrated Arts And Sciences Univ. Of Tokushima

• Takeda Y

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

• MATSUMOTO Takashi

  Faculty of Engineering, Yamanashi University

• SOH Kimiko

  Faculty of Integrated Arts and Sciences, The University of Tokushima

• IMAI Sachihiko

  Suzugamine Women's College

• GOTOH Hisashi

  Faculty of Integrated Arts and Sciences, The University of Tokushima

• Soh K

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

• Soh Kimiko

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

• Takeda Yoshio

  Faculty Of General Arts And Sciences The Tokushima University

• Matsumoto Takashi

  Faculty Of Engineering Department Of Electronic Engineering Yamanashi University

• Matsumoto T

  Department Of Microbiology Tohoku Pharmceutical University

• Gotoh H

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

• Imai S

  Niigata Univ. Pharmacy And Applied Life Sci. Niigata Jpn

• Imai Sachihiko

  Suzugamine Women's College

• Matsumoto T

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

• Matsumoto Takashi

  Faculty Of Agriculture Shinshu University

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