Title: Periplanones
Literature 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).
Derivative Type: Periplanone A
CAS Registry Number: 112709-47-4
CAS Name: (3S,6S,7E,11Z)-9-Methylene-6-(1-methylethyl)-1-oxaspiro[2.9]dodeca-7,11-dien-4-one
Molecular Formula: C15H20O2
Molecular Weight: 232.32
Percent Composition: C 77.55%, H 8.68%, O 13.77%
Properties: Found primarily in excreta of P. americana, it is unstable and gradually rearranges to a biologically inactive compound. uv max (hexane): 220 nm (log e 4.18).
Absorption maximum: uv max (hexane): 220 nm (log e 4.18)
Derivative Type: Periplanone B
CAS Registry Number: 61228-92-0
CAS Name: (1R,2R,5S,6E,10R)-8-Methylene-5-(1-methylethyl)spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2¢-oxiran]-3-one
Additional Names: (-)-periplanone B
Molecular Formula: C15H20O3
Molecular Weight: 248.32
Percent Composition: C 72.55%, H 8.12%, O 19.33%
Properties: More stable and more active than periplanone A, it is found in both the alimentary tract and excreta of P. americana. The ratio of A to B in excreta is 1:10. Crystals, mp 47-50°. [a]D22 -667° (c = 0.13 in n-hexane).
Melting point: mp 47-50°
Optical Rotation: [a]D22 -667° (c = 0.13 in n-hexane)
Derivative Type: (±)-Periplanone B
CAS Registry Number: 70613-99-9
Properties: Crystals, mp 48-50°. uv max (hexane): 226 nm.
Melting point: mp 48-50°
Absorption maximum: uv max (hexane): 226 nm
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