7173. Periplanones
Description and references
Sex pheromones of the American cockroach, Periplaneta americana L., found primarily in the alimentary tract and excreta of the insect. They act as close proximity sex-excitants and function over relatively short distances compared to long range insect sex-attractants. Isoln: D. R. A. Wharton et al., Science 137, 1062 (1962). Improved isolns, identification and proposed structures of periplanone B: C. J. Persoons et al., Tetrahedron Lett. 1976, 2055; E. Talman et al., Isr. J. Chem. 17, 227 (1978); C. J. Persoons et al., J. Chem. Ecol. 5, 221 (1979). Total synthesis and structure of (±) periplanone B: W. C. Still, J. Am. Chem. Soc. 101, 2493 (1979); H. Hauptmann, G. Muhlbauer, Tetrahedron Lett. 27, 1315 (1986); of the (-)-form: T. Kihara et al., ibid. 1343. Absolute configuration of B: M. A. Adams et al., J. Am. Chem. Soc. 101, 2495 (1979). Structural and stereochemical studies of periplanone A: C. J. Persoons et al., J. Chem. Ecol. 8, 439 (1982); H. Hauptmann, G. Muhlbauer, Tetrahedron Lett. 27, 6189 (1986); Y. Shizuri et al., ibid. 28, 1791, 1795 (1987); L. MacDonald et al., Heterocycles 25, 305 (1987). Short synthesis of periplanone A: Y. Shizuri et al., Tetrahedron Lett. 29, 1971 (1988). Use in insecticidal formulations: W. J. Bell et al., Environ. Entomol. 13, 448 (1984); W. J. Bell et al., Pest Control 54, 40 (1986).
