Stereospecific synthesis from non-carbohydrate precursors of the deoxy- and methyl-branched deoxy-sugars L-amicetose, L-mycarose, and L-olivomycose

Abstract

2,3,6-Trideoxy-L-erythro-hexose (L-amicetose)(12), 2,6-dideoxy-3-C-methyl-L-ribo-hexose (L-mycarose)(13), and 2,6-dideoxy-3-C-methyl-L-arabino-hexose (L-olivomycose)(14) have been synthesized from the corresponding lactones (9), (10), and (11), obtained, in turn, upon cleavage with ozone of the aromatic ring of suitable derivatives of the aromatic, C6–C5 optically active methyl diols (1) and (2) prepared from the C6–C3αβ-unsaturated aldehydes and fermenting baker's yeast.