Elysiapyrones from Elysia diomedea. Do such metabolites evidence an enzymatically assisted electrocyclization cascade for the biosynthesis of their bicyclo[4.2.0]octane core?

4 pages, 1 figure, 1 scheme.-- PMID: 15673253 [PubMed].-- Printed version published Feb 3, 2005.Supporting information (Spectral data and experimental procedures) available at: http://pubs.acs.org/doi/suppl/10.1021/ol0477428Biogenetically interesting polypropionate-derived metabolites 1 and 2, featuring an unprecedented skeleton, have been isolated from the sea slug Elysia diomedea. Their enantiomeric character indicates that the current spontaneous electrocyclization cascade biogenetic hypothesis for the bicyclo[4.2.0]octane core must be enzymatically aided. These compounds are isomeric with the 15-nor-9,10-deoxytridachione/15-norphotodeoxytridachione pair of metabolites and encourage speculation about their biosynthetic relationship.This work was supported by the MEC (PPQ2002-02494) and the Canary Islands Government (PI2002/044). The STRI provided support and facilities. Dr. M. Gupta, Dr. J. A. Gómez, J. del Rosario, and D. Macías provided technical support. J. Maté received support from the U.S. NSF, Biological Oceanography Program (OCE- 9711529)