Title: Ajugarins
Literature References: Diterpenes isolated from the leaves of Ajuga remota (Labiatae). Five different ajugarins have been isolated and identified; of these ajugarins I-III possess antifeedant activity against the African army worm, ajugarin-IV has insecticidal activity, ajugarin V is inactive. Isoln and structure of ajugarins I-III: I. Kubo et al., Chem. Commun. 1976, 949; of ajugarin IV: eidem, ibid. 1982, 618; of ajugarin V: eidem, Chem. Lett. 1983, 223. See also: JP Kokai 82 48979 (1982 to Otsuka). X-ray crystal structure of 12-bromoajugarin-I and absolute configuration: I. Kubo et al., Chem. Commun. 1980, 897; 13C-NMR shift data: J. M. Luteijn et al., Org. Magn. Reson. 19, 95 (1982). Synthetic approaches: D. J. Goldsmith et al., J. Org. Chem. 43, 3182 (1978); J. M. Luteijn, Ae. de Groot, Tetrahedron Lett. 1981, 789. Total synthesis of ajugarin-I: S. V. Ley et al., Chem. Commun. 1983, 503.
Derivative Type: Ajugarin-I
CAS Registry Number: 62640-05-5
CAS Name: [1R-(1a,4ab,5b,6a,8a,8aa)]-4-[2-[8-(Acetyloxy)-8a-[(acetyloxy)methyl]octahydro-5,6-dimethylspiro[naphthalene-1(2H),2¢-oxiran]-5-yl]ethyl]-2(5H)furanone
Molecular Formula: C24H34O7
Molecular Weight: 434.52
Percent Composition: C 66.34%, H 7.89%, O 25.77%
Properties: mp 155-157°. uv max (methanol): 212 nm (e 10000).
Melting point: mp 155-157°
Absorption maximum: uv max (methanol): 212 nm (e 10000)
Derivative Type: Ajugarin-II
CAS Registry Number: 62640-06-6
Molecular Formula: C22H32O6
Molecular Weight: 392.49
Percent Composition: C 67.32%, H 8.22%, O 24.46%
Properties: 8-Hydroxy analog of ajugarin I. mp 188-189°.
Melting point: mp 188-189°
Derivative Type: Ajugarin-III
CAS Registry Number: 62640-07-7
Molecular Formula: C24H36O8
Molecular Weight: 452.54
Percent Composition: C 63.70%, H 8.02%, O 28.28%
Properties: 1,1-Dihydroxy analog of ajugarin I. mp 243-245°.
Melting point: mp 243-245°
Derivative Type: Ajugarin-IV
CAS Registry Number: 82225-47-6
Molecular Formula: C23H34O6
Molecular Weight: 406.51
Percent Composition: C 67.96%, H 8.43%, O 23.61%
Properties: mp 119-120.5°. [a]D -57.5° (c = 0.06 in CHCl3). uv max (ethanol): 215 nm (e 17000).
Melting point: mp 119-120.5°
Optical Rotation: [a]D -57.5° (c = 0.06 in CHCl3)
Absorption maximum: uv max (ethanol): 215 nm (e 17000)
Derivative Type: Ajugarin-V
CAS Registry Number: 82231-14-9
Molecular Formula: C22H32O5
Molecular Weight: 376.49
Percent Composition: C 70.18%, H 8.57%, O 21.25%
Properties: mp 217-218°. [a]D -13.5° (c = 0.18 in CHCl3). uv max (ethanol): 210 nm (e 11000).
Melting point: mp 217-218°
Optical Rotation: [a]D -13.5° (c = 0.18 in CHCl3)
Absorption maximum: uv max (ethanol): 210 nm (e 11000)
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