Abstract

An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth has been achieved. Based on the asymmetric methylation of chiral (S)-4-benzyloxazolidin-2-one, the carbon chain of the target molecule was assembled through a C₁+C₁₀+C₄+C₃ procedure. The γ-lactone was transformed into 4-(benzyloxy)butanoic acid and then, with the induction of Evan’s template, a chiral methyl group was introduced to the position of the carboxylic group in 97% de. After reduction and a couple of chemical operations, the designed key intermediate A1 was obtained. The synthesis of another moiety was started from decane-1,10-diol which was selectively protected and oxidized. The long carbon chain was installed according to a Wittig protocol. After deprotection, oxidization, and methylenation, the target molecule was synthesized in 7 linear steps with an overall yield of 30.3%.

中文翻译：

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桃叶蛾的信息素（S）-14-甲基十八烷基-1-烯的新不对称合成

摘要

已实现了桃叶min蛾的性信息素14-甲基-1-十八烯的不对称合成。基于手性（S）-4-苄基恶唑烷丁-2-酮的不对称甲基化，通过C ₁ + C ₁₀ + C ₄ + C ₃ 程序组装目标分子的碳链。将γ-内酯转化成4-（苄氧基）丁酸，然后在Evan's模板的诱导下，将手性甲基引入到97％de的羧基位置。经过还原和几次化学操作后，设计的关键中间体A1 获得了。另一部分的合成从被选择性保护和氧化的癸烷-1,10-二醇开始。长碳链是根据Wittig协议安装的。脱保护，氧化和亚甲基化后，以7个线性步骤合成目标分子，总收率为30.3％。