【摘要】 首次利用甾体皂甙元氧化降解废弃物(R)-4-甲基-δ-戊内酯合成了松叶蜂性信息素(2S,3S,7S)-3,7-二甲基-2-十五醇乙酸酯(2)和丙酸酯(3),甾体皂甙元氧化降解废弃物(R)-4-甲基-δ-戊内酯首先被转化成为性质稳定易保存的(R)-5-澳-4-甲基戊酸甲酯(5),化合物5经过偶联、还原、溴代、环氧加成开环和酰化反应给出目标分子,本研究结果不仅为松叶蜂性信息素化合物2和3提供了一个简洁有效的合成方法,同时也丰富了资源化学(即基于资源性化合物合理利用的有机合成化学)的内涵。更多还原

【Abstract】 The synthesis of the sex pheromones of pine sawflies (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate (2) and its propionate (3) by utilizing the industrial waste,(R)-4-methyl-δ-valerolactone in the deg- radation of steroidal sapogenin was first reported in this paper.(R)-4-Methyl-δ-valerolactone was trans- formed into (R)-methyl 5-bromo-4-methylpentanoate (5) which is a stable and easily reserved reagent.5 then underwent a series of reaction involving coupling,reduction,bromination and addition to epoxide to give target molecules 2 and 3.This research result not only provides a concise synthetic method for (2S,3S,TS)-3,7-dimethylpentadecan-2-yl acetate (2) and propionate (3),but also enrichs the connotation of resource chemistry (the organic synthetic chemistry based on the rational utilization of resource com- pounds).更多还原