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460 



cyclobutanes, cyclobutenes, and cyclobutanones to be generated frou both satu- 

 rated and a,B-unsaturated carbonyl partners. Application of this approach for 

 geminal alkylation to the total synthesis of the constituent of the sex phero- 

 mone of the boll weevil, grandisol, is reported, 



903. Tumlinson, J. H.; Gueldner, R. C; Hardee, D. D. ; Thompson, A. C; Hedin, 

 P. A.; and Minyard, J. P. 1970. The boll weevil sex attractant. In 

 Morton Beroza (ed.). Chemicals Controlling Insect Behavior pp. 41-59, 

 Acad. Press, NY. 



The isolation and identification of four terpenoid compounds from the male boll 

 weevil, which, when properly combined, attract the female, are reported. The 

 structures of all four have been confirmed by synthesis and each is biologically 

 active. The active compounds were isolated from both fecal material and insects 

 by steam distillation and a series of chromatographic separations. They were 

 identified, on the basis of chemical and spectral evidence, as: (I) » cis -2- 

 isopropenyl-1-methylcyclobutaneethanol; (II) , cis- 3,3-dimethyl-A^ '^-cyclohexane- 

 ethanol; (III), cis- 3, 3-dimethyl-A^ '"-cyclohexaneacetaldehyde; (IV), trans- 3, 

 3-dimethyl-A^ »"-cyclohexaneacetaldehyde. These compounds were present in fecal 

 material in concentrations of 0.76, 0.57, 0.05, and 0.06 ppm, respectively. 

 Compounds (I)- (IV) have been synthesized the the synthetic compounds are equally 

 as attractive as the natural substances to females. To produce a substance 

 attractive to females in laboratory bioassays it was necessary to combine com- 

 pounds (I), (II), and either (III) or (IV). Absence of either of the alcohols 

 or both of the aldehydes resulted in an inactive mixture. 



904. ; Gueldner, R. C; Hardee, D. D.; Thompson, A. C; Hedin, P. A.; and 

 Minyard, J. P. 1971. Identification and synthesis of the four compounds 

 comprising the boll weevil sex attractant. J. Org. Chem. 36: 2616-2619. 



Four terpenoid compounds, (+)-cis;-2-isopropenyl-l-m£thylcyclobutaneethanol, (1), 



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