1 フェロモン活性を有する十員環セスキテルペン,(-)-ゲルマフレン-Dおよびペリプラノン-Bの合成研究

概要

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Novel efficient method of synthesizing medium-sized ring systems are developed. Thus the precursors, substituted phenyl-thioacetonitriles(12 and 23), prepared in optically active form from (+)-limonene, were submitted for cyclization with NaN(TMS)_2 in refluxing DME to afford ten-membered ring systems in excellent yield. Although the ambident anion derived from 23 could be alkylated at either α- or γ-position, only the desired α-alkylated product(24) with (E)-olefin was obtained exclusively. (-)-Dihydrogermacrene-D and (-)-germacrene-D, the latter of which is known as sex pheromone mimics of American cockroach (Periplaneta americana), were prepared by employing this method. Feasibility of this procedure to other medium-sized ring was demonstrated by using simple model compounds. Further application to the synthesis of periplanone-B, true sex pheromone of American cockroach will be discussed.
天然有機化合物討論会の論文
1982-09-10