A combined experimental and theoretical study of the supramolecular self-assembly of the natural benzopyran 2,2-dimethyl-3-hydroxy-6-acetyl-chromane and its isomeric benzofuran 10,11-dihydro-10-hydroxytremetone

GIL, DIEGO M.; LIZARRAGA, E.; ECHEVERRÍA, G.A.; PIRO, O.E.; CATALÁN, C.A.N.; BEN ALTABEF, A.

JOURNAL OF MOLECULAR STRUCTURE

ELSEVIER SCIENCE BV

Año: 2017 vol. 1146 p. 164 - 178

0022-2860

Epoxidation of 4HMBA, the main metabolite of the medicinal plant Sencecionutans, produces an unstableepoxide eventually giving rise to a mixture of four derivatives, three of them previously reported asnatural products. The epoxide product easily undergoes an intra-molecular attack of the phenolic hydroxylagainst the epoxide group carbons to produce either a benzofuran or a chromane derivative.When dissolved in methanol-water mixture at room temperature the epoxide is completely solvolyzedto give the corresponding diol (hydrolysis) or vicinal hydroxyl-methoxy (methanolysis) derivative. All thecompounds involved in the above reactions were characterized by IR, Raman, H NMR and UVevisspectroscopies, and by mass spectrometry.