Catalytic asymmetric synthesis of 3,4-disubstituted cyclohexadiene carbaldehydes: formal total synthesis of cyclobakuchiols A and C

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dc.contributor.author Maurya, Vidyasagar
dc.contributor.author Appayee, Chandrakumar
dc.date.accessioned 2018-06-27T10:05:35Z
dc.date.available 2018-06-27T10:05:35Z
dc.date.issued 2018-06
dc.identifier.citation Maurya, Vidyasagar and Appayee, Chandrakumar, "Catalytic asymmetric synthesis of 3,4-disubstituted cyclohexadiene carbaldehydes: formal total synthesis of cyclobakuchiols A and C", Organic Letters, DOI: 10.1021/acs.orglett.8b01667, Jun. 2018. en_US
dc.identifier.issn 1523-7060
dc.identifier.issn 1523-7052
dc.identifier.uri http://dx.doi.org/10.1021/acs.orglett.8b01667
dc.identifier.uri https://repository.iitgn.ac.in/handle/123456789/3775
dc.description.abstract The first catalytic approach for the asymmetric synthesis of 3,4-disubstituted cyclohexadiene carbaldehydes through an inverse-electron-demand Diels�Alder reaction is described. A variety of arylacetaldehydes and ?,?,?,?-unsaturated aldehydes are tested under the mild reaction conditions catalyzed by l-proline to obtain the trans diastereomeric products with good yields and high enantioselectivities. The scope of this methodology is further extended to the asymmetric synthesis 3,4-disubstituted cyclohexane carbaldehydes and their derivatives. The practicality of this method is demonstrated by the gram-scale synthesis. This methodology is successfully applied for the formal total synthesis of cyclobakuchiol A, an antipyretic and anti-inflammatory agent, and cyclobakuchiol C.
dc.description.statementofresponsibility by Vidyasagar Maurya and Chandrakumar Appayee
dc.language.iso en en_US
dc.publisher American Chemical Society en_US
dc.title Catalytic asymmetric synthesis of 3,4-disubstituted cyclohexadiene carbaldehydes: formal total synthesis of cyclobakuchiols A and C en_US
dc.type Article en_US
dc.relation.journal Organic Letters


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