SYNTHESIS OF (2S,3R,1'S,2'S)-STEGOBIOL, A NEW COMPONENT OF THE DRUGSTORE BEETLE PHEROMONE.

Article abstract of DOI:10.1016/S0040-4020(01)82049-4

(2S,3R,1'S,2'S)-Stegobiol 1, a new pheromone component of Stegobium paniceum L., was synthesized with stereocontrol at C-2, C-1' and C-2', starting from ethyl (R)-3-hydroxybutanoate and methyl (S)-3-hydroxypentanoate.The stereochemistry of the naturally occuring 1 was confirmed to be 2S,3R,1'S,2'S by the present synthesis.