SYNTHESIS OF THE SEX-ATTRACTANT OF PINE SAWFLIES (DIPRION SPECIES); (2S,3R,7R)- AND (2S,3R,7S)-3,7-DIMETHYLPENTADECAN-2-Ol

Article abstract of DOI:10.1246/cl.1982.1799

In order to establish the stereochemistry of the sex attractant of diprion species of pine sawflies, two candidate epimers, (2S,3R,7R)- and (2S,3R,7S)-3,7-dimethylpentadecan-2-ol were synthesized by the coupling reaction of optically active C₅ and C₁₂ units.The C₁₂ units, (R)-(-)- and (S)-(+)-1-bromo-2-methylundecane were prepared from (R)-(+)-pulegone.The C₅ unit, (2R,3S)-2-methyl-3-tetrahydropyranoxy-1-tosyloxybutane was derived from (2S,3S)-2-methyl-3-hydroxybutyric acid prepared by the reported procedure.