Natural Product Chemistry, Part 132: Synthesis and Oxidative Cyclisation of 1,3-Dihydroxy-10-methyl-4-(3-methylbut-2-enyl)-9(10H)-acridinone (Glycocitrine-II)

Article abstract of DOI:10.1007/BF00809528

Reaction of 1,3-dihydroxy-10-methyl-9(10H)-acridinone (1) and 1-bromo-3-methylbut-2-ene (mol. ratio 1 : 1) in tetrahydrofuran at 20 deg C in the presence of alumina gave prenylacridinones 2 (glycocitrine-II) and 8 and the diprenylacridinone 9; with an excess of 1-bromo-3-methylbut-2-ene, the prenyldihydroyranoacridinones 12 and 13 were formed.Oxidation of glycocitrine-II (2) with m-chloroperbenzoic acid furnished the furanoacridinone 5 and the pyranoacridinone 6; dehydration of the latter compound gave noracronycine (10).