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.