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Structural and stereochemical revision of isocyanide and isothiocyanate amphilectenes from the Caribbean marine sponge Cribochalina sp. |
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| Authors: | Maria Letizia Ciavatta Margherita Gavagnin Raffaella Puliti Lelio Mazzarella Jamie S. Simpson |
| Affiliation: | a Istituto di Chimica Biomolecolare, C.N.R., 80078 Pozzuoli, Italy b Dipartimento di Scienze Farmaceutiche, Università di Salerno, via Ponte Don Melillo, I-84084 Fisciano, Salerno, Italy c Dipartimento di Chimica, Università “Federico II”, Complesso Universitario di Monte S. Angelo, via Cintia, I-80126 Napoli, Italy d Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, 381 Royal Parade, Parkville Vic. 3052, Australia e School of Molecular and Microbial Sciences, The University of Queensland, Brisbane Qld 4072, Australia |
| Abstract: | The absolute stereochemistry of amphilectene metabolites from Cribochalina sp. has been revised by a detailed NMR spectroscopic study of the Mosher ester derivatives of a related alcohol. The relative stereochemistry of the previously described amphilectenes has been reinvestigated and reassigned on the basis of the X-ray structural analysis carried out on one of them. The structure of a new amphilectene metabolite, which is an isothiocyanato analogue is also presented. |
| Keywords: | Diterpenes NMR Mosher analysis X-ray Stereochemistry Sponges |
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