{"title":"Synthesis of Azocine-Fused Indoles via Gold(I)-Catalyzed Cyclization of Azido-alkynes","authors":"Daiki Hasegawa, Atsuhito Tsuji, Luca C. Greiner, Norihito Arichi, Shinsuke Inuki, Hiroaki Ohno","doi":"10.1021/acs.joc.4c02704","DOIUrl":null,"url":null,"abstract":"Herein, we report a gold(I)-catalyzed cascade cyclization of azido-alkynes bearing an enol ester moiety, leading to indole-fused eight-membered rings. This method allows for the one-step construction of indole and tetrahydroazocin-4-one via an α-imino gold carbene intermediate. The resulting scaffold would be useful for accessing natural products with an eight-membered ring-fused indole moiety.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"65 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2024-12-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02704","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we report a gold(I)-catalyzed cascade cyclization of azido-alkynes bearing an enol ester moiety, leading to indole-fused eight-membered rings. This method allows for the one-step construction of indole and tetrahydroazocin-4-one via an α-imino gold carbene intermediate. The resulting scaffold would be useful for accessing natural products with an eight-membered ring-fused indole moiety.
期刊介绍:
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.