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以十一碳烯醇和碘戊烷为原料,经过苯甲酰基保护、9-硼双环[3.3.1]-壬烷(9-BBN)硼氢化后氧化、氯铬酸吡啶盐(PCC)氧化、Wittig反应、脱苯甲酰基五步反应得到顺-11-十六碳烯-1-醇(Z11-16:OH),五步反应总收率53%.顺-11-十六碳烯-1-醇经PCC氧化或Ac_2O乙酰化分别得到顺-11-十六碳烯-1-醛(Z11-16:Ald)、顺-11-十六碳烯-1-醇乙酸酯(Z11-16:Ac),目标化合物及主要中间体结构经NMR,IR和MS确证.合成方法路线短,操作简便,收率较文献中的方法有较大提高.
Using undecylenol and iodopentane as raw materials, the product was oxidized by hydroboration of benzoyl, 9-borabicyclo [3.3.1] -nonane (9-BBN), chlorinated pyridinium chlorochromate (PCC) Wittig reaction and debenzoyl reaction in 5 steps gave cis -11-hexadecene-1-ol (Z11-16: OH) in 53% overall yield over 5 steps.Cis-11-hexadecene- -alcohol by PCC oxidation or Ac-O acetylation to give cis-11-hexadecene- 1 -aldehyde (Z11-16: Ald), cis- 11 -hexadecen-1-ol acetate : Ac), the target compounds and the structures of the main intermediates were confirmed by NMR, IR and MS.The synthesis route was short, the operation was simple and the yield was greatly improved compared with the literature methods.