Synthetic Studies on Lignans and Related Compounds. VI. Photochemical Rearrangement of β-Apolignans

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概要

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• The photochemistry of the β-apolignan (1) was investigated, and a specific rearrangement was found to occur on irradiation of 1. The photoproduct was identified as a tetrahydrocycloprop (a) indene (2b) based on an unambiguous synthesis of the dihydro product (3b) derived from its hydrogenolysis. Similar irradiation of taiwanin A gave two isomeric tetrahydrocycloprop (a) indenes (10a and 10b) via the cyclization into β-apolignans followed by their degenerate rearrangement. Consequently, this type of phototransformation was found to be a common feature of β-apolignans irrespective of ring substituents, and was characterized as a vinyl-aryl di-π-methane rearrangement. Mechanistic aspects of the rearrangement are briefly described.

• 社団法人日本薬学会の論文
• 1978-05-25

著者

• 百瀬 雄章

  Faculty of Pharmaceutical Sciences, Kinki University

• 金井 健一

  Faculty Of Pharmaceutical Sciences Osaka University

• 百瀬 雄章

  富山医薬大・薬

• 中村 健

  Faculty of Pharmaceutical Sciences, Osaka University

• 百瀬 雄章

  (present Address)faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Osaka University

• 中村 健

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Kanazawa University

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