Heliespirone A. The first member of a novel family of bioactive sesquiterpenes

Tetrahedron Letters

Volumn 39, Issue 5-6, 1998, Pages 427-430

  Macías, Francisco A ^a   Varela, Rosa M ^a   Torres, Ascensión ^a   Molinillo, José Ma G ^a  

^a UNIVERSITY OF CÁDIZ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

HELIESPIRONE A; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT; STEREOCHEMISTRY; SUNFLOWER;

HELIANTHUS; HELIANTHUS ANNUUS;

EID: 0032576802     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10538-X     Document Type: Article

References (16)

1. 1. Part 11 in the series "Allelopathic studies in cultivar species" for part 10 see Macías, F.A.; Varela, R.M.; Torres, A.; Oliva, R.M. and Molinillo, J.M.G. Phytochemistry 1998, 48, in press.
2. 2. Macías, F.A.; Varela, R.M.; Torres, A; Molinillo, J.M.G. in Allelopathy in Pests Management for Sustainable Agriculture, Vol 2 (Ed. S.S. Narwal; P. Tauro) Scientific Publishers, Jodhpur, India 1996, pp. 77-92.
3. 3. Leather, G.R. Plant Soil 1987, 98, 17-23.
4. 4. a) Leather, G.R. J. Chem. Ecol. 1983, 9, 983-989.
5. b) Saggese, E.J.; Foglia, T.A.; Leather, G.; Thompson, M.P.; Bills, D.D.; Hoagland, P.D. in The Chemistry of Allelopathy (Ed. A.C. Thompson) ACS Symposium Series No. 268, Washington D.C., U.S.A. 1985, pp. 99-112.
6. 5. Macías, F.A.; Varela, R.V.; Torres, A.; Molinillo, J.M.G.; Castellano, D. in Recent Advances on Allelopathy. A Science for The Future, Vol I (Eds. F.A. Macías; J.M.G. Molinillo; J.C.G. Galindo; H.G. Cutler) CAB Publishers, U.K. 1997, pp. 000-000.
7. 6. a) Macías, F.A.; Varela, R.M.; Torres, A.; Molinillo, J.M.G. Phytochemistry 1993, 34, 669-674.
8. b) Macías, F.A.; Torres, A., Molinillo, J.M.G.; Varela, R.M.; Castellano, D. Phytochemistry 1996, 43, 1205-1215.
9. 7. Macías, F.A.; Molinillo, J.M.G.; Torres, A.; Varela, R.M.; Castellano, D. Phytochemistry 1997, 45, 683-687.
10. 8. Macías, F.A.; Molinillo, J.M.G.; Torres, A.; Varela, R.M. J. Chem. Ecol. 1997, 23, 0000-0000.
11. 9. a) Macías, F.A.; Varela, R.M.; Torres, A.; Molinillo, J.M.G. Tetrahedron Letters 1993, 34, 1999-2002.
12. b) Macías, F.A.; Molinillo, J.M.G.; Varela, R.M.; Torres, A. J. Org. Chem. 1994, 59, 8261-8266.
13. 14,14=1.3 Hz.
14. 3) δ: 87.6 (C-1), 201.5 (C-2), 137.0 (C-3), 153.4 (C-4), 179.5 (C-5), 51,8 (C-6), 135.3 (C-7), 57.1 (C-8), 31.9 (C-9), 86.7 (C-10), 70.1 (C-11), 28.3* (C-12), 25.3* (C-13), 118.4 (C-14), 15.9 (C-15). * May be interchanged.
15. 12. Stewart, J.J.P. J. Comput. Chem. 1989, 10, 209,221. Molecular orbital calculations were carried out using PM3 Hamiltonian as implemented in MOPAC 6.0. Geometries were fully optimized using the PRECISE keyword.
16. 13. Varela, R.M. "Allelochemicals of The Variety Cultivar Sunflower SH-222. Heliannuols and Heliespirones Two Novel Families of Sesquiterpenes". Doctoral Thesis. University of Cádiz, Spain, 1996.