Stereoselective Synthesis Directed Toward Polyoxygenated Compounds: Synthesis of a 3-Deoxy-D-galacto-nonulosonic Acid (KDN) Equivalent

Angkana Herunsalee; Minoru Isobe; Sanislaw Pikul; Toshio Goto

doi:10.1055/s-1991-20679

Synlett 1991; 1991(3): 199-202
DOI: 10.1055/s-1991-20679

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Stereoselective Synthesis Directed Toward Polyoxygenated Compounds: Synthesis of a 3-Deoxy-D-galacto-nonulosonic Acid (KDN) Equivalent

Angkana Herunsalee^* , Minoru Isobe, Sanislaw Pikul, Toshio Goto

^*Laboratory of Organic Chemistry, School of Agriculture, Nagoya University, Chikusa, Nagoya 464-01, Japan

Abstract

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A general synthetic method directed toward highly oxygenated natural products was studied, which involved asymmetric oxidation and differentiation of the oxygen functionality. The method concluded the synthesis of a KDN equivalent lactone [(1S,2S,3R,4R)-1-(3,3-dibromo-2-oxotetrahydrofur-5-yl)-1,2,3,4,5-pentaacetoxypentane).

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