Asymmetric Synthesis of Corey Lactone and Latanoprost
Asymmetric Synthesis of Corey Lactone and Latanoprost
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科里内酯和拉坦前列素的不对称合成
DOI：
10.1002/ejoc.202001063
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发表时间：
2020
影响因子：
2.8
通讯作者：
Hayashi Yujiro
中科院分区：
文献类型：
--
作者：
Umekubo Nariyoshi;Hayashi Yujiro
Corey内酯在152分钟内以50%的总收率在一锅中通过锅和时间经济的方式合成。抗青光眼新药拉坦前列素经七步反应、五步纯化，总收率25%。关键反应之一是二苯基脯氨醇硅醚催化的3-（二甲基苯基硅基）丙烯醛和4-氧代-2-戊烯酸乙酯的不对称多米诺Michael/Michael反应，即[3+2]环加成反应，该反应构建了近光学纯形式的核取代环戊酮衍生物。
Corey lactone was synthesized in a single pot within 152 minutes in a 50 % overall yield via pot and time economical manner. Latanoprost, an antiglaucoma blockbuster drug, was also synthesized via seven pot reaction with five purifications in a 25 % total yield. One of the key reactions is asymmetric domino Michael/Michael reaction, formal [3+2] cycloaddition reaction, of 3‐(dimethylphenylsilyl)propenal and ethyl 4‐oxo‐2‐pentenoate, catalyzed by diphenylprolinol silyl ether, which constructed the core substituted cyclopentanone derivative with nearly optically pure form.