Jianfeng Li, Ankun Zhou, Xiaoting Wang, Wenping Zhang, Qixin Zhou, Ning Li
{"title":"(2R,6R)-羟基炔诺酮胺的简明合成。","authors":"Jianfeng Li, Ankun Zhou, Xiaoting Wang, Wenping Zhang, Qixin Zhou, Ning Li","doi":"10.1021/acs.joc.4c01502","DOIUrl":null,"url":null,"abstract":"<p><p>A concise synthesis of (<i>2R,6R</i>)-hydroxynorketamine was accomplished in eight steps, starting from commercially available materials. This synthesis features a cerium chloride-enhanced Stork-Danheiser reaction, an asymmetric reduction of ketone by the Corey-Bakshi-Shibata reaction, a signature Overman rearrangement, and a facial selective dihydroxylation of an electronically deficient olefin by RuCl<sub>3</sub>/NaIO<sub>4</sub>. The overall yield is 7.3% with 94.5% <i>ee</i>.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16909-16916"},"PeriodicalIF":3.3000,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A Concise Synthesis of (<i>2R,6R</i>)-Hydroxynorketamine.\",\"authors\":\"Jianfeng Li, Ankun Zhou, Xiaoting Wang, Wenping Zhang, Qixin Zhou, Ning Li\",\"doi\":\"10.1021/acs.joc.4c01502\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>A concise synthesis of (<i>2R,6R</i>)-hydroxynorketamine was accomplished in eight steps, starting from commercially available materials. This synthesis features a cerium chloride-enhanced Stork-Danheiser reaction, an asymmetric reduction of ketone by the Corey-Bakshi-Shibata reaction, a signature Overman rearrangement, and a facial selective dihydroxylation of an electronically deficient olefin by RuCl<sub>3</sub>/NaIO<sub>4</sub>. The overall yield is 7.3% with 94.5% <i>ee</i>.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"The Journal of Organic Chemistry\",\"volume\":\" \",\"pages\":\"16909-16916\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-11-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"The Journal of Organic Chemistry\",\"FirstCategoryId\":\"88\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.joc.4c01502\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/11/1 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"88","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01502","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/11/1 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
A Concise Synthesis of (2R,6R)-Hydroxynorketamine.
A concise synthesis of (2R,6R)-hydroxynorketamine was accomplished in eight steps, starting from commercially available materials. This synthesis features a cerium chloride-enhanced Stork-Danheiser reaction, an asymmetric reduction of ketone by the Corey-Bakshi-Shibata reaction, a signature Overman rearrangement, and a facial selective dihydroxylation of an electronically deficient olefin by RuCl3/NaIO4. The overall yield is 7.3% with 94.5% ee.
期刊介绍：
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
