{"title":"从海洋海绵 Halichondria melanodocia 中分离出的吲哚生物碱的合成","authors":"Gordon W. Gribble, Stephen W. Wright","doi":"10.1016/j.tet.2024.134368","DOIUrl":null,"url":null,"abstract":"<div><div>We describe the first successful synthesis of the indole alkaloid isolated from the marine sponge <em>Halichondria melanodocia</em>, using the previously unreported nickel catalyzed cross electrophile coupling of an α-bromoketone to a <em>sp</em><sup><em>2</em></sup> iodide to provide a convergent synthesis of the carbon framework without concomitant olefin migration. The indole alkaloid was thus synthesized in two steps from known compounds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134368"},"PeriodicalIF":2.1000,"publicationDate":"2024-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of the indole alkaloid isolated from the marine sponge Halichondria melanodocia\",\"authors\":\"Gordon W. Gribble, Stephen W. Wright\",\"doi\":\"10.1016/j.tet.2024.134368\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>We describe the first successful synthesis of the indole alkaloid isolated from the marine sponge <em>Halichondria melanodocia</em>, using the previously unreported nickel catalyzed cross electrophile coupling of an α-bromoketone to a <em>sp</em><sup><em>2</em></sup> iodide to provide a convergent synthesis of the carbon framework without concomitant olefin migration. The indole alkaloid was thus synthesized in two steps from known compounds.</div></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":\"169 \",\"pages\":\"Article 134368\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-11-10\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040402024005490\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402024005490","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Synthesis of the indole alkaloid isolated from the marine sponge Halichondria melanodocia
We describe the first successful synthesis of the indole alkaloid isolated from the marine sponge Halichondria melanodocia, using the previously unreported nickel catalyzed cross electrophile coupling of an α-bromoketone to a sp2 iodide to provide a convergent synthesis of the carbon framework without concomitant olefin migration. The indole alkaloid was thus synthesized in two steps from known compounds.
期刊介绍：
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
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