Novel Bioactive Cubé Insecticide Constituents: Isolation and Preparation of 13-homo-13-Oxa-6a,12a-dehydrorotenoids

Journal of Organic Chemistry

Volumn 62, Issue 2, 1997, Pages 350-353

  Fang, Nianbai ^a   Casida, John E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008904099     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961604h     Document Type: Article

References (17)

1. Negherbon, W. O. Handbook of Toxicology. Volume III: Insecticides; W. B. Saunders Co.: Philadelphia, PA, 1959; p 661.
2. Fukami, H.; Nakajima, M. In Naturally Occurring Insecticides; Jacobson, M., Crosby, D. G., Eds.: Dekker, New York, 1971; p 71.
3. Hollingworth, R. M.; Ahammadsahib, K. I. Rev. Pestic. Toxicol. 1995, 3, 277.
4. Pezzuto, J. M. Recent Adv. Phytochem. 1995, 29, 19.
5. Kostova, I.; Ognyanov, I. F.E.C.S. Int. Conf. Chem. Biotechnol. Biol. Act. Nat. Prod., [Proc.] 3rd; VCH: Weinheim, 1985 (Pub. 1987); Vol. 4, p 350.
6. 3 (δ, 300 MHz). J values are given in Hz. Compound 1: 7.84 (1H, d, J = 8.5, H-11), 6.77 (1H, s, H-1), 6.51 (1H, d, J = 8.5, H-10), 6.45 (1H, s, H-4), 5.24 (1H, dd, J = 8.1,9.8, H-5′), 5.07 (1H, s, H-7′), 4.94 (1H, s, H-7′), 4.94 (1H, m, H-6a), 4.62 (1H, dd, J = 3.0,12.0, H-6), 4.18 (1H, d, J = 12.0, H-6), 3.84 (1H, d, J = 4.0, H-12a), 3.81 (3H, s, 2-OMe), 3.77 (3H, s, 3-OMe), 3.32 (1H, dd, J = 9.8,15.7, H-4′), 2.95 (1H, dd, J = 8.1,15.7, H-4′), 1.77 (3H, s, H-8′). Compound 3: 8.45 (1H, s, H-1), 8.13 (1H, d, J = 8.6, H-11), 6.93 (1H, d, J = 8.6, H-10), 6.55 (1H, s, H-4), 5.41 (1H, dd, J = 7.9,9.8, H-5′), 5.14 (1H, s, H-7′), 5.00 (2H, s, H-6), 4.98 (1H, s, H-7′), 3.96 (3H, s, 2-OMe), 3.87 (3H, s, 3-OMe), 3.53 (1H, dd, J = 9.8,15.8, H-4′), 3.19 (1H, dd, J = 7.9,15.8, H-4′), 1.81 (3H, s, H-8′).
7. 3 (δ, 75 MHz). Compound 1: 188.7 (C-12), 167.2 (C-9), 157.8 (C-7a), 149.4 (C-3), 147.3 (C-4a), 143.8 (C-2), 142.9 (C-6′), 129.8 (C-11), 113.2 (C-11a), 112.8 (C-8), 112.3 (C-7′), 110.5 (C-1), 104.8 (C-1a), 104.7 (C-10), 100.9 (C-4), 87.7 (C-5′), 72.2 (C-6a), 66.1 (C-6), 56.2 (2-OMe), 55.7 (3-OMe), 44.5 (C-12a), 31.2 (C-4′), 17.0 (C-8′). Compound 3: 174.1 (C-12), 164.7 (C-9), 155.9 (C-7a), 152.1 (C-6a), 148.3 (C-3), 146.1 (C-4a), 143.9 (C-2), 142.7 (C-6′), 127.7 (C-11), 118.8 (C-1a), 112.9 (C-12a), 112.8 (C-7′), 111.5 (C-11a), 110.5 (C-8), 110.0 (C-10), 108.5 (C-1), 100.3 (C-4), 87.8 (C-5′), 64.7 (C-6), 56.2 (2-OMe), 55.8 (3-OMe), 31.4 (C-4′), 17.0 (C-8′).
8. Crombie, L.; Lown, J. W. J. Chem. Soc. 1962, 775.
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11. Luyengi, L.; Lee, I.-S.; Mar, W.; Fong, H. H. S.; Pezzuto, J. M.; Kinghorn, A. D. Phytochemistry 1994, 36, 1523.
12. Ollis, W. D.; Rhodes, C. A.; Sutherland, I. O. Tetrahedron 1967, 23, 4741.
13. 1 = 0.0682 (calculated based on 2522 observed (> 2s(I)) data).
14. Parkin, S.; Moezzi, B.; Hope, H. J. Appl. Crystallogr. 1995, 28, 53.
15. Carlson, D. G.; Weisleder, D.; Tallent, W. H. Tetrahedron 1973, 29, 2731.
16. Wood, E.; Latli, B.; Casida, J. E. Pestic Biochem. Physiol 1996, 54, 135.
17. Cohen, E.; Quistad, G. B.; Casida, J. E. Life Sci. 1996, 58, 1075.