120663-14-1Relevant articles and documents
STEREOSELECTIVE SYNTHESIS OF BOTH ENANTIOMERS OF DISPARLURE, THE SEX PHEROMONE OF THE GYPSY MOTH, FROM D-GLUCOSE
Achmatowicz, Osman,Sadownik, Andrzej,Bielski, Roman
, p. 553 - 564 (2007/10/02)
1,2-O-Isopropylidene-α-D-xylopentodialdo-1,4-furanose readily avalaible from D-glucose was transformed in two Wittig reactions and glycol cleavage into a (Z) and (E) mixture of (7R,8R)-8-benzyloxy-7-hydroxy-2-methyl-9-octadecenes.From this chiral synthon both enantiomers of disparlure, (7R,8S)-(+)- and (7S,8R)-(-)-7,8-epoxy-2-methyloctadecane were obtained in four and three steps, respectively.