NEW STRATEGY IN THE SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO), 2-DEOXY-KDO AND THIOGLYCOSIDE OF KDO

To take advantage of synthetic intermediates on the way to KDO, we dev eloped a new strategy based on an aqueous hetero Diels-Alder reaction with a water-soluble diene derived from D-glyceraldehyde, followed by a dihydroxylation of the newly created double bond. The stereoselectiv ities of these reactions were investigated to give rise to 2-deoxy-KDO , which was sulfenylated via the enolate to yield beta-thioglycoside, the hydrolysis of which led to KDO.