Synthesis of Insect Sex Pheromones and Their Homologues; (Z)-6-Alkenyl Acetates from the Wittig Reaction
Synthesis of Insect Sex Pheromones and Their Homologues; (Z)-6-Alkenyl Acetates from the Wittig Reaction
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昆虫性信息素及其同系物的合成；
DOI：
10.1271/bbb1961.42.1963
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发表时间：
1978
期刊：
影响因子：
--
通讯作者：
C. Hirano
中科院分区：
文献类型：
--
作者：
M. Horiike;M. Tanouchi;C. Hirano
许多夜行性飞蛾的雌性性信息素已被证明主要是具有Z构型的乙酸烯基酯。')迄今为止，金属催化剂上的炔烃氢化'-')已被广泛用于烯基信息素的合成。最近，格氏反应以及维蒂希反应由于具有容易获得几何纯烯烃的优点而引起了该领域工作者的广泛关注。鉴于双键的几何形状实质上影响烯基信息素的生物活性，立体选择性的这一特征至关重要。本文作者采用了正链烷醛与(c)-羟基烷基)和((邻-乙酰氧基烷基)三苯基溴化鏻的Wittig反应，希望探索一种空间控制合成烯基信息素的通用路线。作者在此描述了(Z)-6-烯基乙酸酯的成功合成，特别强调了反应参数的优化，特别是所选溶剂系统的优化。
Female sex pheromones of many nocturnal moths have proved mostly to be alkenyl acetates with Z-configuration.') To date, the hydrogenation of alkynes over metallic catalysts'-') has been widely employed for the synthesis of alkenyl pheromones. Recently, the Grignard couplings) as well as the Wittig reactions-'' attracted much attention of workers in this field because of the advantage of permitting easy access to geometrically pure alkenes. This feature of stereoselectivity is of utmost importance in view of the fact that it is the geometry of double bond that substantially affects the biological activity of alkenyl pheromones. The present authors adopted the Wittig reaction of n-alkanals with (c)-hydroxyalkyl)and ((o-acetoxyalkyl) triphenylphosphonium bromides in a hope to exploit a general route for sterically controlled synthesis of alkenyl pheromones. Authors describe here the successful synthesis of (Z)-6-alkenyl acetates with special emphasis on the optimization of reaction parameters, in particular, of solvent systems of choice.