Cong So Tran, Moonsang Yoon, Long Duc Le, Seoyeong Kim, Huiae Kim, Jisu Kim, Long Huu Nguyen, Minseob Koh, Hwayoung Yun
{"title":"Rapid Access to cis-1,3-Dialkylindanes: Asymmetric Formal Syntheses of epi-Mutisianthol and epi-Jungianol","authors":"Cong So Tran, Moonsang Yoon, Long Duc Le, Seoyeong Kim, Huiae Kim, Jisu Kim, Long Huu Nguyen, Minseob Koh, Hwayoung Yun","doi":"10.1055/a-2249-2326","DOIUrl":null,"url":null,"abstract":"Concise and strategically unique asymmetric formal syntheses of epi-mutisianthol and epi-jungianol are presented. A novel disconnection approach is introduced to complement previous intramolecular cyclopentannulation strategies. Noteworthy features include: (a) the control of the stereogenic benzylic carbon center through 1,3-chirality transfer from chiral indenols via the Johnson-Claisen rearrangement, which yields advanced indene-containing γ,δ-unsaturated esters, and (b) the diastereoselective construction of the cis-1,3-dialkylindane backbone via catalytic hydrogenation of the resulting indene. This approach presents a remarkable method for synthesizing structurally intriguing indane motifs.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"80 16","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2249-2326","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
Concise and strategically unique asymmetric formal syntheses of epi-mutisianthol and epi-jungianol are presented. A novel disconnection approach is introduced to complement previous intramolecular cyclopentannulation strategies. Noteworthy features include: (a) the control of the stereogenic benzylic carbon center through 1,3-chirality transfer from chiral indenols via the Johnson-Claisen rearrangement, which yields advanced indene-containing γ,δ-unsaturated esters, and (b) the diastereoselective construction of the cis-1,3-dialkylindane backbone via catalytic hydrogenation of the resulting indene. This approach presents a remarkable method for synthesizing structurally intriguing indane motifs.
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