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As part of our ongoing interest in the synthesis of benzannelated heterocycles from o-substituted benzylfurans, recyclization of [o-(hydroxymethyl)aryl]difurylmethanes was studied. It was shown that, under acidic conditions, the o-hydroxymethyl group in these compounds acts as a nucleophile and tetracyclic isochromene derivatives are formed via a recyclization-cyclization tandem sequence. Alternatively, these compounds can be synthesized by reduction of the corresponding isochromone derivatives with lithium aluminum hydride. The potent biologically active analogues of cannabinoids were also obtained by interaction of isochromone derivatives with excess of methylmagnesium iodide.

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9-furylnaphtho[2,3-b]furans. -A first example concerning the recyclization of 2 furan cycles in (I) is described. It results in a synthesis of angular furylnaphthofurans (II). -(MEL'CHIN, V. V.; BUTIN*, A. V.; Tetrahedron Lett. 47 (2006) 25, 4117-4120; Res. Inst. Heterocycl. Compd. Chem., Kuban State Technol. Univ., Krasnodar 350072, Russia; Eng.) -Mais 39-121