PHEROMONES OF INSECTS AND THEIR ANALOGS. XXI. SYNTHESIS OF ALK-8Z-EN-1-OLS AND THEIR ACETATES FROM A FUNCTIONALLY DIFFERENTIATED PRODUCT OF OZONOLYSIS OF CYCLOOCTENE

Article abstract of DOI:10.1007/BF00598421

Dodec-8Z-en-1-ol (VIII) and tetradec-8Z-en-1-ol (IX) and the corresponding acetates (X and IX) - components of the sex pheromones of many species of Lepidoptera - have been synthesized from cyclooctene (I) in three stages.The ozonolysis of (I) ( -70 deg C, CH2Cl2-MeOH), NaHCO3; -20 deg C, Ac2O/Et3N) led to methyl 8-oxooctanoate (II).The DNPH of (II), (III), mp 59-61 deg C.The coupling of (II) with n-C3H17CH=PPh3 (IV) or with n-C5H11CH=PPh3 (V) (-70 deg C , 2h; 25 deg C, 15h, Ar) gave the methyl esters of dodec-8Z-enoic (VI) and tetradec-8Z-enoic (VII) acids, respectively.The reduction of (VI) and (VII) <(i-Bu)2AlH, 0 deg C, 2h; 25 deg C, 15h> gave the corresponding alcohols (VIII) and (IX) by the acetylation (Ac2O-Py, 25 deg C, 24h) of which, (X) and (XI) , were obtained.The yields (percent): (II) 80, (VI) 45, (VII) 60, (VIII) 95, (IX) 90, (X) 75, (XI) 74.The IR and PMR spectra of compounds (II) and (VI-XI) are given.