Synthesis of lactones using substituted benzoic anhydride as a coupling reagent
Synthesis of lactones using substituted benzoic anhydride as a coupling reagent
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DOI：
10.1038/nprot.2007.316
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发表时间：
2007-10
期刊：
影响因子：
14.8
通讯作者：
Isamu Shiina;H. Fukui;Akane Sasaki
中科院分区：
文献类型：
--
作者：
Isamu Shiina;H. Fukui;Akane Sasaki
该方案描述了用于合成29元大环内酯的程序。在刘易斯酸或碱性催化剂的促进下，混合酸酐法是一种简便、有效的合成羧酸酯和内酯的方法。由于反应快速进行，以产生具有高化学选择性的单体化合物，该协议是非常强大的合成不仅是巨大的内酯，但也高度紧张的环状化合物，如中等大小的内酯。取代苯甲酸酐促进的内酯化反应的显著效率已经在许多天然复杂分子的合成中显示出来。完成该方案需要大约19小时：0.5小时用于建立反应，13.5小时用于反应，5小时用于分离和纯化。
This protocol describes a procedure for the synthesis of a 29-membered macrolactone. The facile mixed-anhydride method is very effective for the preparation of carboxylic esters and lactones using substituted benzoic anhydrides by the promotion of Lewis acid or basic catalysts under mild reaction conditions. Owing to the reaction rapidly proceeding to produce the monomeric compounds with high chemoselectivity, the protocol is quite powerful for the synthesis of not only the giant-sized lactones but also the highly strained cyclic compounds such as medium-sized lactones. The remarkable efficiency of the lactonizations promoted by the substituted benzoic anhydrides has been already shown in the synthesis of many natural complex molecules. It takes approximately 19 h to complete the protocol: 0.5 h to set up the reaction, 13.5 h for the reaction and 5 h for isolation and purification.