Formal Synthesis of Spirovetivane Sesquiterpenes

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Other Title
  • スピロベチバン型セスキテルペンの形式合成
  • スピロベチバンガタ セスキテルペン ノ ケイシキ ゴウセイ

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Abstract

Oxidation of sulfide (4) derived from tosylate (7), with m-chloroperbenzoic acid gave sulfoxide (5). Diels-Alder reaction of 5 with E-2-trimethylsiloxy-1, 3-pentadiene gave a mixture of 6b and 6c, which were successively treated with MeCu-TMSCl-TMEDA and Pd(OAc)2 to give enones (11a) and (11b). Enone (11b) was converted to the key intermediate (3) for the synthesis of spirovetivane sesquiterpenes via dithioacetal (14).

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 108 (7), 635-640, 1988

    The Pharmaceutical Society of Japan

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