Synthesis of 6-Methoxy-1,1,10-trimethyl-1,2,3,4-tetrahydroanthracene, a Synthetic Intermediate of a Linear Abietane Diterpene, Umbrosone

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概要

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• Methyl 13-acetyl-12-methoxy-8,11,13-podocarpatrien-18-oate, prepared from (+)-dehydroabietic acid, was converted into methyl 12-methoxy-7-oxo-5,8,11,13-podocarpatetraen-18-oate (9) by a series of reactions : haloform reaction, decarboxylation, Jones oxidation, and dehydrogenation. Reduction of 9 with sodium borohydride, followed by treatment of the resulting 7-hydroxy compound with boron trifluoride etherate, afforded a rearranged ester, methyl 6-methoxy-1,10-dimethyl-1,2,3,4-tetrahydroanthracene-1-carboxylate. This was further converted into 6-methoxy-1,1,10-trimethyl-1,2,3,4-tetrahydroanthracene (14) by means of the following reactions : lithium aluminum hydride reduction, pyridinium chlorochromate oxidation, and Huang-Minlon reduction. Compound 14 was finally converted into the desired orthoquinone (1) according to the procedure of Ghosh and Ghatak. The synthetic 1 was shown to be identical with natural umbrosone by spectral comparisons.

• 社団法人日本薬学会の論文
• 1996-03-15

著者

• 高石 喜久

  徳島大院薬

• USUI Shuji

  Department of Clinical Radiology, Faculty of Health Sciences, Hiroshima International University

• 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

• IMAI Sachihiko

  Suzugamine Women's College

• 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

• Usui Shuji

  Department Of Chemistry Faculty Of Science Hiroshima University

• 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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