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Synthesis 2000; 2000(13): 1930-1935
DOI: 10.1055/s-2000-8228
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Synthesis of Both Enantiomers of a Novel Sesquiterpene Isolated from the Pheromone Gland of a Stink Bug, Tynacantha marginata Dallas

Shigefumi Kuwahara*
  • *Laboratory of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan; Fax +81(22)7 17 87 83; E-mail: skuwahar@biochem.tohoku.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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Synthesis of both enantiomers of a novel sesquiterpene, isolated as the putative sex pheromone of a Brazilian predatory stink bug (Tynacantha matginata Dallas) and proposed to have an unprecedented tricyclic carbon framework, was accomplished through an intramolecular Diels - Alder cyclization of a single optically active triene intermediate and separation of a pair of structural isomers derived from the resulting cycloadducts.

cyclopentadienes - Diels - Alder reactions - pheromones - terpenoids - total synthesis

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