The reaction of C-alkylation of eudesmanolide (–)-α-santonin

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dc.contributor.author Merkhatuly, N.
dc.contributor.author Iskanderov, A.N.
dc.contributor.author Omarova, А.Т.
dc.contributor.author Vojtíšek, P.
dc.contributor.author Zhokizhanova, S.K.
dc.date.accessioned 2019-08-23T08:28:04Z
dc.date.available 2019-08-23T08:28:04Z
dc.date.issued 2019-06-28
dc.identifier.citation Merkhatuly, N. The reaction of C-alkylation of eudesmanolide (–)-α-santonin / N. Merkhatuly, A.N. Iskanderov, А.Т. Omarova [et al.] // Қарағанды универисетінің хабаршысы. Химия сериясы.=Вестник Карагандинского университета. Серия Химия.=Bulletin of the Karaganda University. Chemistry series. – 2019. – № 2. – P. 14-18. ru_RU
dc.identifier.issn 2518-718X
dc.identifier.issn 2663-4872
dc.identifier.uri http://rep.ksu.kz//handle/data/7296
dc.description.abstract This article is concerned with sesquiterpene γ-lactones of the eudesman structure, which is promising class of natural organic compounds and characterized by a wide spectrum of physiological activity. Stereoselective synthesis of new practically significant 4α(ethyl)-3-keto-trans-eudesm-1(2),5(6)-diene-6,12-olide(C4-α-ethylsantonin) was carried out at room temperature in argon atmosphere by interaction of eudesmanolide (–)-α-santonin and an organohalide in presence of a strong base: tert-butyl-potassium: dimethylsulfoxide: tert-butyl alcohol. The yield was 50 %. The spatial structure of the synthesized C4-α-ethyl-santonin was established by 1H NMR-, 2D NMR (COZY, NOESY), mass spectrometry and X-ray analysis. According to the results of X-ray analysis there has been found that the condensed six-membered C4-α-ethyl-santonin cycles are trans-articulated (CH3-10, β-oriented), the ethyl group at C-4 has the α-configuration, and the conformation of six-membered eudesmanolide is characterized as distorted chair-chair. Thus, combination of application in the work of modern physico-chemical and spectroscopic research methods allowed characterization of the structure and properties of the compounds obtained. ru_RU
dc.language.iso en ru_RU
dc.publisher Ye.A.Buketov Karaganda State University Publishing house ru_RU
dc.relation.ispartofseries Қарағанды универисетінің хабаршысы. Химия сериясы.=Вестник Карагандинского университета. Серия Химия.=Bulletin of the Karaganda University. Chemistry Series.;№ 2(94)/2019
dc.subject sesquiterpene γ-lactone ru_RU
dc.subject cross-conjugated ru_RU
dc.subject eudesmanolide ru_RU
dc.subject α-santonin ru_RU
dc.subject alkylation ru_RU
dc.subject keto-eudesmane ester ru_RU
dc.subject stereoselectivity ru_RU
dc.subject electrophilic rearrangements ru_RU
dc.title The reaction of C-alkylation of eudesmanolide (–)-α-santonin ru_RU
dc.title.alternative Эвдесманолид (‒)-α-сантониннің С-алкилдеу реакциясы ru_RU
dc.title.alternative Реакция С-алкилирования эвдесманолида (‒)-α-сантонина ru_RU
dc.type Article ru_RU


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