Synthesis and glycosidase inhibitory activity of 7-deoxycasuarine
Reaction of 1,4-anhydro-2,3,5-tri-O-benzyl-1-deoxy-1-imino-D-arabinitol N-oxide (8) with allyl alcohol produced a 3.6:1 mixture of the two pyrrolo[1,2-b]isoxazole derivatives 13 and 14. The major adduct 13 was converted to 7-deoxycasuarine (7), a potent, specific, and competitive inhibitor of amyloglucosidase from Rhizopus mold (see Table).
Keywords: Functionalized cyclic nitrones ; hydroxylated pyrrolizidines ; cycloaddition reactions ; polyhydroxylated pyrrolizidines ; azomethine ; ylides ; n-oxides ; d-ribose ; indolizidines ; (+)-australine ; australine
Univ Sevilla, Fac Quim, Dept Quim Organ, E-41071 Seville, Spain. Heriot Watt Univ, Dept Chem, Edinburgh EH14 4AS, Midlothian, Scotland. Ecole Polytech Fed Lausanne, Inst Chim Mol & Biol, BCH, CH-1015 Lausanne, Switzerland.
Record created on 2005-11-09, modified on 2016-08-08