2863. Deguelin

Nomenclature

CAS number: 522-17-8
(7aS-cis)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6′,5′-e]pyran-7(7aH)-one.
C23H22O6; mol wt 394.42.
C 70.04%, H 5.62%, O 24.34%.

Description and references

From roots of Tephrosia toxicaria Pers., leaves of Tephrosia vogelii Hook f., Leguminosae, and from derris and cubé roots: H. L. Haller, F. B. LaForge, J. Am. Chem. Soc. 56, 2415 (1934); E. Brierly, H. J. Smith, J. Pharm. Pharmacol. 20, 840 (1968). Structure: Clark, J. Am. Chem. Soc. 54, 3000 (1932). Stereoselective synthesis: P. B. Anzeveno, J. Org. Chem. 44,2578 (1979). Total synthesis of racemate: Fukami et al., Agric. Biol. Chem. 25, 252 (1961); Omokawa, Yamashita, ibid. 38, 1731 (1974). Stereochemical studies: Djerassi et al., J. Chem. Soc. 1961, 1448.

Chemical structure

Properties

Yellow oil, [α]D27 -97.2° (c = 0.2 in benzene).

Derivative

(±)-Form.

Properties

Pale green crystals, mp 171°. Practically insol in water. Sol in alc.

Caution

Irritates skin. Inhalation may cause fatal pulmonary damage.

Use

Insecticide.