New 8-Oxabicyclo[3.2.1]oct-6-en-3-one Derivatives with Plant Growth Regulatory Activity

Journal of Agricultural and Food Chemistry

Volumn 46, Issue 3, 1998, Pages 1173-1176

  Demuner, Antonio J ^a   Barbosa, Luiz C A ^a   Veloso, Dorila P ^b  

^a FEDERAL UNIVERSITY OF VIÇOSA   (Brazil)

^b FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

Cucumber; Oxyallyl cation; Plant growth regulators; Sorghum

Indexed keywords

CUCUMIS SATIVUS; EUDICOTYLEDONS; LILIOPSIDA; SORGHUM BICOLOR;

EID: 0141719465     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf970413s     Document Type: Article

References (19)

1. Barbosa, L. C. A. A new synthetic approach to the pseudoguaianolide skeleton via oxyallyl cation chemistry. Ph.D. Thesis, University of Reading, 1991.
2. Barbosa, L. C. A.; Mann, J. The use of diethylzinc for the generation of oxyallyl carbocation from polybromo ketones and their reactions with substituted furans. Synthesis 1996, 31-33.
3. Barbosa, L. C. A.; Demuner, A. J.; Mann, J.; Pilo-Veloso, D. Novel rearrangement of 2α-isopropyl-8-oxabicyclo[3.2.1]oct-6-eae producing the monoterpene 3-hydroxyphellandral. J. Chem. Soc., Perkin Trans, 1 1993, 585-587.
4. Barbosa, L. C. A.; Demuner, A. J.; Borges, E. E. L.; Mann, J. Synthesis and evaluation of the plant growth regulatory activity of 8-oxabicyclo[3.2.1]oct-6-en-3-one derivatives. J. Braz. Chem. Soc. 1997, 8, 19-27.
5. Briggs, D. E. Gibberellin-like activity of helminthosporol and helminthosporic acid. Nature 1966, 210, 418-419.
6. Copping, L. G. Crop Protection Agents from Nature. Natural Products and Analogues; Royal Society of Chemistry: Cambridge, U.K., 1996.
7. De Mayo, P.; Spencer, E. Y.; White, R. W. Helminthosporal, the toxin from Helminthosporium sativum: isolation and caracterization. Can. J. Chem. 1961, 39, 1608-1612.
8. Demuner, A. J. Síntese de derivados do ácido 6α,7β-dihidroxivouacapan-17β-óico e de análogos do ácido helmintospórico, visando estudos de atividades analgésica e reguladora do crescimento de plantas. Ph.D. Thesis, University of Belo Horizonte, 1996.
9. Demuner, A. J.; Barbosa, L. C. A.; Pilo-Veloso, D.; Ferreira-Alves, D. L.; Howarth, O. W. Structure and plant growth regulatory activity of new diterpenes from Pterodon polygalaeflorus. J. Nat. Prod. 1996, 59, 770-772.
10. Demuner, A. J.; Barbosa, L. C. A.; Pilo-Veloso, D. Cicloadições [3+4] via cations oxialílicos: aplicações em sínteses orgânicas. Quim. Nova 1997, 20, 18-29.
11. Einhellig, F. A.; Schan, M. K.; Rasmunsen, J. A. Synergistic effects of four cinnamic acid compounds on grain sorghum. Plant Growth Regul. 1983, 1, 251-258.
12. Fairclough, B. Pesticide chemistry. Chem. Int. 1994, 16, 210-214.
13. Godfrey, C. R. A. Agrochemicals from Natural Products. Dekker: New York, 1995.
14. Gomes, F. P. Curso de Estatística Experimental, 13th ed.; Nobel: Piracicaba, 1990.
15. Mander, L. N.; Turner, J. V.; Coombe, B. G. Synthetic ptant growth regulators. I. The synthesis of (±)-14-norhelminthosporic acid and related compounds. Aust. J. Chem. 1974, 27, 1985-2000.
16. Mann, J. The synthetic utility of oxyallyl cations. Tetrahedron 1986, 42, 4611-4659.
17. Mann, J.; Holland, H. J. Cycloaddition reactions of polysubstituted furans with oxyallyl carbocations. Tetrahedron 1987, 43, 2533-2542.
18. Mann, J.; Overton, H. J. Synthetic utility of oxyallyls: preparation of an analogue of helminthosporic acid. Tetrahedron Lett. 1985, 26, 6133-6136.
19. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals; Pergamon Press: Oxford, U.K., 1988.