75. Enantiomeric 3,7-Dimethylocta-1,7-dienes as Useful Chiral Building Blocks. A New Access to Both Optical Antipodes of Natural (E)-3,7-Dimethyloct-2-ene-1,8-diol and (E)-3,7-Dimethyloct-2-ene-1,8-dicarboxylic Acid

Article abstract of DOI:10.1002/hlca.19900730322

Ozonolysis of the easily available monoterpenoids (-)-1 and (+)-1 leads in high yield to the keto-aldehydes (-)-4 and (+)-4, which serve as convenient intermediates for efficient new routes to both optical antipodes of the naturally occuring octene-diol (E)-2 (Monarch butterfly secretion product) and octene-dicarboxylic acid (E)-3 (Callosobruchus chinensis sex pheromone).All steps proceed with almost complete retention of configuration, ensuring the synthesis of the target compounds with high optical purity.