Sythesis of Two Macrolide Pheromones of the Rusty Grain Beetle, Cryptolestes ferrugineus (Stephens)

Article abstract of DOI:10.1021/jo00173a043

Two macrolide pheromones for Cryptolestes ferrugineus (Stephens), the rusty grain beetle, have been synthesized.Synthesis of 4,8-dimethyl-4(E),8(E)-decadienolide (1) was achived by intramolecular alkylation of an ω-bromo (phenylthio)acetate derived from geraniol by reaction with (phenylthio)acetyl choride and allylic functionalization of the 8(E)-methyl.Macrolide 1 was also synthesized by intramolecular esterification of an ω-hydroxy acid derived from geraniol by formal addition of acetate to tetrahydroparanyl-protected 8(E)-bromogeraniol.Synthesis of the second macrolide, 11-methyl-3(Z)-undecenolide (2), also involved intramolecular esterification of the appropriate hydroxy acid.The chiral center of 2 was introduced via chiral propylene oxides while the Z unsaturation was introduced by P-2 nickel reduction of the appropriate alkyne.Both chiral isomers of 2 were synthesized.