Rearrangement approaches to cyclic skeletons. II. Structural revision and total synthesis of (.+-.)-isosesquicarene, a (3-6) fused-ring sesquiterpene.

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概要

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• The <I>exo</I>-7-(4-methyl-3-pentenyl) derivative of 3-carene (<B>1a</B>), the original structure reported for (±)-isosesquicarene, was synthesized starting from tropone, and it was found that <B>1a</B> is not identical with natural isosesquicarene. The structure of isosesquicarene was reinterpreted as <I>endo</I>-7-(4-methyl-3-pentenyl) derivative of 3-carene (<B>1b</B>). The first total synthesis of (±)-isosesquicarene, <B>1b</B>, has been accomplished on the basis of the photochemical transformation of 4-methylbicyclo[3.2.2]nona-3,6-dien-2-one into the 7-<I>exo</I>-methylbicyclo[4.1.0]hept-2-ene.

• 公益社団法人 日本化学会の論文

著者

• Yamada Jun-ichi

  Department Of Electronics Faculty Of Engineering Kobe University:(present Address) The Musashino Ele

• Uyehara Tadao

  Department Of Applied Chemistry Faculty Of Engineering Utsunomiya University

• Kato Tadahiro

  Department of Applied Microbial Technology, Kumamoto Institute of Technology

• Bohlmann Ferdinand

  Institut fur Organische Chemie, Technische Universtat Berlin

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