Collect. Czech. Chem. Commun. 1992, 57, 159-168

Total Synthesis of Protected Form of Fungi Metabolite Cortalcerone

Barbara Szechner and Osman Achmatowicz

Institute of General Chemistry, Warsaw Agricultural University, 02-528 Warsaw, Poland


Synthesis of methyl 4,5-dideoxy-D,L-hex-4-enos-2-ulopyranosid-3-ulose ethylene acetal, derivative of the first natural sugar with dihydropyranone moiety, from 5-acetoxymethylfurfural is described. It was shown that 1,3-transposition of the allylic alcohol in the dihydropyran ring, a key step of the synthesis, can be carried out via an intermediate allylic selenoxide with excellent regio- and stereoselectivity.