利用甾体皂甙元氧化降解废弃物(R)-4-甲基-δ-戊内酯合成松叶蜂主要性信息素(2S,3S,7S)-3,7-二甲基-2-十五醇乙酸酯和丙酸酯

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-溴-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.

Practical Synthesis of the Main Sex Pheromones of Pine Sawflies(2S,3S,7S)-3,7-Dimethylpentadecan-2-ol Esters by Utilizing(R)-4-Methyl-δ-Valerolactone Obtained from the Industrial Waste

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 degradation of steroidal sapogenin was first reported in this paper. (R)-4-Methyl-δ-valerolactone was transformed 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,7S)-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 compounds).