Collect. Czech. Chem. Commun.
1992, 57, 159-168
https://doi.org/10.1135/cccc19920159
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
Abstract
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.
