文献类型：期刊文献

英文题名：Practical synthesis of canthaxanthin

作者：Pi, Shiqing[1,2];Xi, Meiyang[1];Deng, Liping[1];Xu, Huiting[1];Feng, Chengjie[1];Shen, Runpu[1,2];Wu, Chunlei[1]

机构：[1]Shaoxing Univ, Dept Chem & Chem Engn, Shaoxing 312000, Zhejiang, Peoples R China;[2]Zhejiang Med Co Ltd, Xinchang Pharmaceut Factory, Xinchang 312500, Zhejiang, Peoples R China

年份：2020

卷号：17

期号：2

起止页码：493

外文期刊名：JOURNAL OF THE IRANIAN CHEMICAL SOCIETY

收录：SCI-EXPANDED(收录号：WOS:000513235100021)、、Scopus(收录号：2-s2.0-85074098960)、WOS

基金：This study was supported by the Public Projects of Zhejiang Province of China (No. LGG19B020002).

语种：英文

外文关键词：Canthaxanthin; Wittig-Horner condensation; Total synthesis; Phosphonate

外文摘要：In this study, a novel route for the total synthesis of canthaxanthin is described. The synthesis is firstly based on an epoxidation of alpha-ionone with metachloroperbenzoic acid to afford the epoxide, followed by conversion of the epoxide to 3-hydroxyl-beta-ionone in the presence of sodium methoxide. Next, 3-hydroxyl-C14-aldehyde was obtained by a Darzens condensation with 4-hydroxyl-beta-ionone and methyl chloroacetate, which can be converted to 3-hydroxyl-C15-phophonate via a Wittig-Horner condensation with tetraethyl methylenebisphosphonate. Then, a Wittig-Horner condensation with 3-hydroxyl-C15-phosphonate and C10-trienedial resulted in 4,4 '-dihydroxyl-beta-carotene, followed by an oxidation afforded the target product canthaxanthin. The overall yield of this route is 37% from alpha-ionone. The synthetic steps are easily operated and are practical for the large-scale production.