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Communication | Regular issue | Vol 27, No. 7, 1988, pp.1561-1564
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4491
Acid Catalyzed Dimerization of the Pyranocoumarin Xanthoxyletin: Formation of a "Diels-Alder" Dimer Analogous to the Paraensidimerines

Sharon E. Parker, Alexander I. Gray, and Peter G. Waterman*

*Phytochemistry Research Labratories, Department of Pharmacy (Pharm. Chem.), University of Strathclyde, Glasgow G1 1XW, Scotland, U.K.


Acid-catalyzed dimerization of xanthoxyletin has given, in low yield, a dimeric compound which has been identified as a Diels-Alder addition product in which the C-4’ and C-3’ positions of one monomer have linked, respectively, with one of the C-2’ methyls and C-4’ of the other. While a similar dimerization reaction is known in a number of pyranoquinolone alkaloids from the Rutaceae this is the first report of its occurrence among pyranocoumarins.