Dora-Marina Gutierrez-Avella, Michèle Bertrand, Robert Nouguier
{"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}
引用次数: 0
Abstract
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.