Dora-Marina Gutierrez-Avella, Michèle Bertrand, Robert Nouguier
{"title":"从d-葡萄糖和d-甘露糖衍生的多取代1,6-二烯的tosyl自由基介导环化的立体诱导","authors":"Dora-Marina Gutierrez-Avella, Michèle Bertrand, Robert Nouguier","doi":"10.1016/S1387-1609(01)01251-8","DOIUrl":null,"url":null,"abstract":"<div><p>Polysubstituted 1,6-dienes <strong>1</strong> and <strong>6</strong>, derived from 6-iodo-<span>d</span>-manno- and <span>d</span>-glucopyranosides through Boord fragmentation and subsequent olefination, undergo cyclization upon addition of TsSePh under radical conditions. Functionalized cyclopentitols result from tributyltin hydride mediated reduction of the adducts. A tentative rationalization of steroinduction is given, and a comparison is made with related data in the literature.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 6","pages":"Pages 453-459"},"PeriodicalIF":0.0000,"publicationDate":"2001-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01251-8","citationCount":"0","resultStr":"{\"title\":\"Stereoinduction in the tosyl radical-mediated cyclization of polysubstituted 1,6-dienes derived from d-glucose and d-mannose\",\"authors\":\"Dora-Marina Gutierrez-Avella, Michèle Bertrand, Robert Nouguier\",\"doi\":\"10.1016/S1387-1609(01)01251-8\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Polysubstituted 1,6-dienes <strong>1</strong> and <strong>6</strong>, derived from 6-iodo-<span>d</span>-manno- and <span>d</span>-glucopyranosides through Boord fragmentation and subsequent olefination, undergo cyclization upon addition of TsSePh under radical conditions. Functionalized cyclopentitols result from tributyltin hydride mediated reduction of the adducts. A tentative rationalization of steroinduction is given, and a comparison is made with related data in the literature.</p></div>\",\"PeriodicalId\":100305,\"journal\":{\"name\":\"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry\",\"volume\":\"4 6\",\"pages\":\"Pages 453-459\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2001-06-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01251-8\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S1387160901012518\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1387160901012518","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Stereoinduction in the tosyl radical-mediated cyclization of polysubstituted 1,6-dienes derived from d-glucose and d-mannose
Polysubstituted 1,6-dienes 1 and 6, derived from 6-iodo-d-manno- and d-glucopyranosides through Boord fragmentation and subsequent olefination, undergo cyclization upon addition of TsSePh under radical conditions. Functionalized cyclopentitols result from tributyltin hydride mediated reduction of the adducts. A tentative rationalization of steroinduction is given, and a comparison is made with related data in the literature.
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