Synthesis of enantiomers of sulcatol

Abstract

The synthesis of R-(−)- and S-(+)-6-methylhept-5-en-2-ol (sulcatol) is reported from commercially available carbohydrate precursors. The synthesis of the R-(−) enantiomer utilizes the four hydroxy function of 2-deoxy-D-ribose as a preformed precursor of the chiral secondary alcohol centre. The five hydroxy group of L-fucose provides the basis for a similar synthesis of the S(+) enantiomer. These isomers are to be used to test the aggregation response of Gnathotricus sulcatus, a northwestern American timber pest.