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Oxazinins from toxic mussels: isolation of a novel oxazinin and reassignment of the C-2 configuration of oxazinin-1 and -2 on the basis of synthetic models |
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| Authors: | Patrizia Ciminiello Carmela Dell'Aversano Martino Forino Federico Umberto Santelia Emmanuel N Pitsinos |
| Institution: | a Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli ‘Federico II’, Via D. Montesano 49, 80131 Napoli, Italy b Natural Product Synthesis and Bioorganic Chemistry Laboratory, Institute of Physical Chemistry, NCSR ‘Demokritos’, PO Box 60228, GR 153 10 Ag. Paraskevi, Greece c Chemistry Laboratories, Agricultural University of Athens, Iera Odos 75, GR 118 55 Athens, Greece |
| Abstract: | The analysis of a batch of toxic mussels (Mytilus galloprovincialis) from the Northern Adriatic Sea led to the isolation of a novel oxazinin, oxazinin-4. Its structure including the relative stereochemistry has been elucidated through extensive NMR analysis. A synthetic route to oxazinins has been crucial in establishing the absolute stereochemistry of oxazinin-4 and for reassigning the absolute C-2 configuration of oxazinin-1 and -2 previously isolated from toxic shellfish and stereostructurally characterized. |
| Keywords: | Oxazinins Adriatic shellfish Natural products Synthetic models Mytilus galloprovincialis NMR spectroscopy |
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