Alfonso G. Rubia , Mateo M. Salgado , Carlos T. Nieto , Alejandro Manchado , David Díez , Francisca Sanz , Narciso M. Garrido
{"title":"Asymmetric synthesis of tert-butyl ((1R,4aR,8R,8aR)-1-hydroxyoctahydro-1H-isochromen-8-yl)carbamate","authors":"Alfonso G. Rubia , Mateo M. Salgado , Carlos T. Nieto , Alejandro Manchado , David Díez , Francisca Sanz , Narciso M. Garrido","doi":"10.1016/j.tetasy.2017.10.005","DOIUrl":null,"url":null,"abstract":"<div><p><span>The asymmetric synthesis of methyl (</span><em>E</em>)-4-((1<em>R</em>,2<em>S</em>,3<em>R</em>)-3-amino-2-((<em>E</em>)-2-methoxycarbonyl-eten-1-yl)cyclohexyl)but-2-enoate <strong>14</strong> has been achieved from dimethyl (2<em>E</em>,7<em>E</em>)-nona-2,7-dienedioate <strong>2</strong>. A key step is the asymmetric synthesis of 1-hydroxyoctahydro-1<em>H</em>-isochromene derivative <strong>5</strong><span><span> whose X-ray analysis corroborated the stereochemistry of the new stereocenters. The asymmetric synthesis of the isochromenyl </span>acetate derivative </span><strong>11</strong> shows the potential of this methodology for fused cyclohexanic system heterocyclic synthesis.</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 10","pages":"Pages 1394-1400"},"PeriodicalIF":0.0000,"publicationDate":"2017-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.10.005","citationCount":"2","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron, asymmetry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0957416617303671","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Chemistry","Score":null,"Total":0}
引用次数: 2
Abstract
The asymmetric synthesis of methyl (E)-4-((1R,2S,3R)-3-amino-2-((E)-2-methoxycarbonyl-eten-1-yl)cyclohexyl)but-2-enoate 14 has been achieved from dimethyl (2E,7E)-nona-2,7-dienedioate 2. A key step is the asymmetric synthesis of 1-hydroxyoctahydro-1H-isochromene derivative 5 whose X-ray analysis corroborated the stereochemistry of the new stereocenters. The asymmetric synthesis of the isochromenyl acetate derivative 11 shows the potential of this methodology for fused cyclohexanic system heterocyclic synthesis.
期刊介绍：
Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry.
The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.
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
