27 ワールブルガナールの全合成

概要

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Warburganal, a potent antifeedant against the army worms S.exempta and S.littoralis was synthesized stsrting from decalone derivatives(1) or (2). Introduction of C-1 unit at C8 of decalone derivative was achieved by the reaction of tosylhydrazone 4 with n-Butyllithium followed by trapping of vinyl anion with DMF. Hydroxy group was introduced at C9 by the treatment of diacetate (6) with selenium dioxide. Triol was successfully oxidized to warburganal by the modified Corey-Kim reaction, in which the counter ion (Cl^-) was replaced by tetrafluoro borate ion. Other synthetic routes to warburganal are also discussed.
天然有機化合物討論会の論文
1979-09-20