Biomimetic synthesis of xuxuarines E alpha and E beta: Structure revision of Rzedowskia bistriterpenoids
| Contribuinte(s) |
Universidade Estadual Paulista (UNESP) |
|---|---|
| Data(s) |
20/05/2014
20/05/2014
15/02/2008
|
| Resumo |
Reaction of pristimerin with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) resulted in a biomimetic-type coupling leading to xuxuarines E alpha and E beta and not the previously reported Rzedowskia bistriterpenoids I and II suggesting that the structures proposed for these natural products need revision. A product obtained in this reaction by an unusual Diels-Alder addition followed by retro-Diels-Alder-type elimination was characterized as pristimerin dicyanophenalenedione. Complete H-1, and C-13 NMR spectral assignments of xuxuarines Ea and Eb have been made by the application of 1D and 2D NMR techniques. (c) 2007 Elsevier Ltd. All rights reserved. |
| Formato |
1884-1889 |
| Identificador |
http://dx.doi.org/10.1016/j.bmc.2007.11.008 Bioorganic & Medicinal Chemistry. Oxford: Pergamon-Elsevier B.V. Ltd, v. 16, n. 4, p. 1884-1889, 2008. 0968-0896 http://hdl.handle.net/11449/26095 10.1016/j.bmc.2007.11.008 WOS:000254080900027 |
| Idioma(s) |
eng |
| Publicador |
Pergamon-Elsevier B.V. Ltd |
| Relação |
Bioorganic & Medicinal Chemistry |
| Direitos |
closedAccess |
| Tipo |
info:eu-repo/semantics/article |
