10037. Warburganal

Nomenclature

CAS number: 62994-47-2
(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-Octahydro-1-hydroxy-5,5,8a-trimethyl-1,2-naphthalenedicarboxaldehyde.
C15H22O3; mol wt 250.33.
C 71.97%, H 8.86%, O 19.17%.

Description and references

Drimane sesquiterpene with antifeedant activity against the African army worm. Biological activity includes plant growth regulation, cytotoxic, antimicrobial and molluscicidal properties. Isoln from Warburgia ugandensis, Canellaceae and structure: I. Kubo et al., Chem. Commun. 1976, 1013. Relationship between structure and antifeedant activity: K. Nakanishi, I. Kubo, Isr. J. Chem. 16, 28 (1977). Synthesis of (±)-warburganal: S. P. Tanis, K. Nakanishi, J. Am. Chem. Soc. 101, 4398 (1979); T. Nakata et al., ibid. 4400; A. S. Kende, T. J. Blacklock, Tetrahedron Lett. 1980, 3119; P. A. Wender, S. L. Eck, ibid. 1982, 1871; D. M. Hollinshead et al., J. Chem. Soc. Perkin Trans. 1 1983, 1579. See also: JP Kokai 80 136238, and JP 80 136240 (both 1980 to Inst. Phys. Chem. Res.); JP Kokai 81 43236 (1981 to Suntory Ltd.); JP Kokai 83 38232 (1983 to Teikoku Zoki). Synthesis of ()-warburganal: H. Okawara et al., Tetrahedron Lett. 1982, 1087.

Chemical structure

Properties

mp 98-99°. uv max (methanol): 224 nm (ε 6300). [α]D21 260° (c = 0.350 in CHCl3).