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Asymmetric synthesis of (S)-dihydrokavain from l-malic acid

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dc.contributor.author Durucasu, Inci
dc.contributor.author Eskici, Mustafa
dc.contributor.author Kabak, Yalcin
dc.contributor.author Karanfil, Abdullah
dc.contributor.author Ozer, M. Sabih
dc.date.accessioned 2022-08-17T07:09:54Z
dc.date.available 2022-08-17T07:09:54Z
dc.date.issued 2018
dc.identifier.uri http://doi.org/10.1080/00397911.2018.1489057
dc.identifier.uri http://earsiv.odu.edu.tr:8080/xmlui/handle/11489/2698
dc.description.abstract A practical and efficient asymmetric synthesis of (S)-dihydrokavain from known ethyl (S)-2-hydroxy-4-phenylbutanoate which is, in turn, readily available from l-malic acid as a cheap chiral pool material is described using regioselective ring-opening of the 1,2-cyclic sulfate with lithium-3,3,3-triethoxypropiolate and subsequent HgO/H2SO4-mediated lactonization as the key steps. Its opposite enantiomer (R)-dihydrokavain was also synthesized from d-malic acid using the same sequences of reactions for the purpose of optical purity determination. en_US
dc.language.iso eng en_US
dc.publisher TAYLOR & FRANCIS INC, 530 WALNUT STREET, STE 850, PHILADELPHIA, PA 19106 USA en_US
dc.relation.isversionof 10.1080/00397911.2018.1489057 en_US
dc.rights info:eu-repo/semantics/openAccess en_US
dc.subject 1; 2-Cyclic sulfates; dihydrokavain; lactonization; triethylorthopropiolate en_US
dc.title Asymmetric synthesis of (S)-dihydrokavain from l-malic acid en_US
dc.type article en_US
dc.relation.journal SYNTHETIC COMMUNICATIONS en_US
dc.contributor.department Ordu Üniversitesi en_US
dc.contributor.authorID 0000-0003-2948-4216 en_US
dc.identifier.volume 48 en_US
dc.identifier.issue 18 en_US
dc.identifier.startpage 2382 en_US
dc.identifier.endpage 2390 en_US


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