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001-es BibID:BIBFORM043273
Első szerző:Jia, Rui
Cím:Biscembranoids Formed from an [alpha],[beta]-Unsaturated [gamma]-Lactone Ring as a Dienophile : Structure Revision and Establishment of Their Absolute Configurations Using Theoretical Calculations of Electronic Circular Dichroism Spectra / Rui Jia, Tibor Kurtán, Attila Mándi, Xiao-Hong Yan, Wen Zhang, Yue-Wei Guo
Dátum:2013
ISSN:0022-3263
Megjegyzések:Four new biscembranoids, bislatumlides C-F (1-4), were isolated from the Hainan soft coral Sarcophyton latum. Their structures were elucidated by detailed analysis of spectroscopic data and by comparison with reported data of related derivatives, leading to the structure revision of co-occurring bislatumlides A (5) and B (6) at the C-21 configuration. The absolute configurations of bislatumlides C and E (1 and 3) were determined by TDDFT calculations of their solution ECD spectra, allowing the configurational assignment of the related bislatumlides D and F (2 and 4) and A and B (5 and 6) as well. Bislatumlides A-F (1-6) represent the only biscembranoids formed by the undescribed coupling pattern of Diels-Alder cycloaddition between the ?1(2) double bond involving an [alpha],[beta]-unsaturated [gamma]-lactone ring as a dienophile group and a trisubstituted conjugated ?21(34)/?35(36)-butadiene moiety. An endo-cycloaddition gave 1, 2, 5, and 6, whereas an exocycloaddition produced 3 and 4. This is the first report of exo-addition dicembranoids from marine sources and from nature. Bislatumlides C and E (1, 3) could be used as ECD reference compounds in the determination of absolute configuration for related derivatives.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Megjelenés:Journal of Organic Chemistry. - 78 : 7 (2013), p. 3113-3119. -
További szerzők:Kurtán Tibor (1973-) (vegyész, angol szakfordító) Mándi Attila (1981-) (vegyész, német szakfordító) Yan, Xiao-Hong Zhang, Wen Guo, Yue-Wei
Pályázati támogatás:K105871, K81701
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