■^fKT-. '■ fefy.t ff;r^K;:rrpr,r-riVfr, rym 



350 



689. Mori, K. 1978. Synthesis of the both enantiomers of grandisol, the 

 boll weevil pheromone. Tetrahedron 34: 915-20. 



Optically active forms of grandisol (2-isopropenyl-l-methylcyclobutane ethanol, 



I and I') were synthesized from optically active 5-carboxybicyclo[3.2.0]heptan- 



2-one (2 and its antipode) , obtained by resolving the racemate. The optical 



purities of the synthetic products were determined by the NMR studies using a 



chiral shift reagent and shown to be 80%. The [a]_ values of our synthetic / 



grandiols were ±20° (after correction) in accord with Magnus's synthetic (+)- 



grandisol (+ 18.5" after correction) and differed from that reported for the 



natural pheromone C+SOilO"). 



690. ; Tamade, S.; and Hedir, P. A. 1978. (-)-grandisol, the antipode of 

 the boll weevil pheromone, is biologically active. Naturwissenschaften 

 65: 653-654. 



(IR, 2S)-(+)-Grandisol (JL) is one of the four pheromone components isolated 



from male boll weevils, Anthonomus grandis Boheman [1,2]. We synthesized its 



antipode and found it to be as biologically active as an isolated pheromone 



component. Antipodes of bioactive chiral molecules were generally believed 



to be devoid of biological activity. This dogma wa.. proved to be untrue in 



the present case. "" 



*- 



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■ »^-«'--'ir ii-**i- -^ i^'im.-i^^.'i-^^r^" ''\ ■*•* - ^vO'-v-Ato^li . 



