Collect. Czech. Chem. Commun.
1983, 48, 1659-1668
https://doi.org/10.1135/cccc19831659
Hydroxylation of 6-substituted 2,7-dioxabicyclo[3.2.0]hept-3-enes. The synthesis of analogs of 3-deoxy-DL-streptose
Tadeusz Kozluk and Alexander Zamojski
Institute of Organic Chemistry, Polish Academy of sciences, 01-224 Warszawa, Poland
Abstract
Hydroxylation of 6-substituted 2,7-dioxabicyclo[3.2.0]hept-3-enes (I, XIV and XV) with m-chloroperoxybenzoic acid occurs mainly from the exo side and leads to the corresponding 3-m-chlorobenzoates of trans-3,4-diols (VI, XVIII and XXII). Hydroxylation of substrates XIV and XV with potassium permanganate leads to 3-deoxy-3-C-formyl-DL-arabino-aldofuranoses. Epimerization at the formyl group-bearing carbon atom occurs during the reorganization of dihydroxylated dioxabicycloheptanes in basic medium.
