Jiquilpane hydrocarbon skeleton generated by two successive Wagner-Meerwein rearrangements of longipinane derivatives

Journal of Natural Products

Volumn 65, Issue 11, 2002, Pages 1540-1546

  Román, Luisa U ^a   Cerda García Rojas, Carlos M ^a   Guzmán, Ramón ^a   Armenta, Concepción ^a   Hernández, Juan D ^a   Joseph Nathan, Pedro ^b  

^a UNIVERSIDAD MICHOACANA DE SAN NICOLÁS DE HIDALGO   (Mexico)

^b DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

7,8,9 TRIACETYLOXYJIQUILP 3(12) ENE; 7,8,9 TRIACETYLOXYLONGIPINAN 1 OL; 7,8,9 TRIACETYLOXYURUAP 3(12) ENE; DEUTERIUM; HYDROCARBON; JIQUILPANE; LONGIPINANE DERIVATIVE; SESQUITERPENOID; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOISOMERISM; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SESQUITERPENES; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 0036854786     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0201570     Document Type: Article

References (27)

1. Hernández, R.; Catalán, C. A. N.; Joseph-Nathan, P. Rev. Acad. Colomb. Cienc. Ex. Fis. Nat. 1998, 22, 229-279; available on: http://www.accefyn.org.co/PubliAcad/Periodicas/83/83(229)/ 83(nathan).html.
2. Cerda-García-Rojas, C. M.; Pereda-Miranda, R. In Stevia: The Genus Stevia; Medicinal and Aromatic Plants-Industrial Profiles, Vol. 19; Kinghorn, A. D., Ed.; Taylor & Francis: London 2002; Chapter 5, pp 86-118.
3. Román, L. U.; Hernández, J. D.; del Río, R. E.; Bucio, M. A.; Cerda-García-Rojas, C. M.; Joseph-Nathan, P. J. Org. Chem. 1991, 56, 1938-1940.
4. Román, L. U. Hernández, J. D.; Cerda-García-Rojas, C. M.; Domínguez- López, R. M.; Joseph-Nathan, P. J. Nat. Prod. 1992, 55, 577-588.
5. Román, L. U.; Zepeda, L. G.; Morales, N. R.; Hernández, J. D.; Cerda-García-Rojas, C. M.; Joseph-Nathan, P. J. Nat. Prod. 1995, 58, 1808-1816.
6. Román, L. U.; Zepeda, L. G.; Morales, N. R,; Flores, S.; Hernández, J. D.; Cerda-García-Rojas, C. M.; Joseph-Nathan, P. J. Nat. Prod. 1996, 59, 391-395.
7. Román, L. U.; Morales, N. R.; Hernández, J. D.; Cerda-García-Rojas, C. M.; Zepeda, L. G.; Flores-Sandoval, C. A.; Joseph-Nathan, P. Tetrahedron 2001, 57, 7269-7275.
8. Cerda-García-Rojas, C. M.; Flores-Sandoval, C. A.; Román, L. U.; Hernández, J. D.; Joseph-Nathan, P. Tetrahedron 2002, 58, 1061-1068.
9. Román, L. U.; del Rio, R. E.; Hernández, J. D.; Cerda, C. M.; Cervantes, D.; Castañeda, R.; Joseph-Nathan, P. J. Org. Chem. 1985, 50, 3965-3972.
10. Cremer, D.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354-1358.
11. Zotov, A.; Palyulin, V.; Zefirov, N. RICON Program Version 5.05; Moscow State University: Moscow, Russia, 1994.
12. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Part A: Structure and Mechanisms; Plenum Press: New York, 1990; pp 313-319.
13. Pietro, W. J.; Francl, M. M.; Hehre, W. J.; DeFrees, D. J.; Pople, J. A.; Binkley, J. S. J. Am. Chem. Soc. 1982, 104, 5039-5048.
14. Joseph-Nathan, P.; Mejia, G.; Abramo-Bruno, D. J. Am. Chem. Soc. 1979, 101, 1289-1291.
15. Aydin, R.; Wesener, J. R.; Günther, H.; Santillan, R. L.; Garibay, M. E.; Joseph-Nathan, P. J. Org. Chem. 1984, 49, 3845-3847.
16. Román, L. U.; del Rio, R. E.; Hernández, J. D.; Joseph-Nathan, P.; Zabel V.; Watson, W. H. Tetrahedron 1981, 37, 2769-2778.
17. Bauer, K.; Garbe, D.; Surburg, H. Common Fragrance and Flavor Materials: Preparation, Properties, and Uses; Wiley-VCH: Weinheim, 1998; pp 73-195.
18. Kula, J.; Masarweh, A. Flavour Frag. J. 1998, 13, 277-278.
19. Takasu, K.; Mizutani, S.; Noguchi, M.; Makita, K.; Ihara, M. Org. Lett. 1999, 1, 391-393.
20. Takasu, K.; Mizutani, S.; Noguchi, M.; Makita, K.; Ihara, M. J. Org. Chem. 2000, 65, 4112-4119.
21. Strongman, D. B.; Miller, J. D.; Calhoun, L.; Findlay, J. A.; Whitney, N. J. Bot. Mar. 1987, 30, 21-26.
22. Wang, Y. Z.; Miller, J. D. Phytopath. Z. 1988, 122, 118-125.
23. König, G. M.; Wright, A. D. Planta Med. 1996, 62, 193-211.
24. Sheldrick, G. M. Programs for Crystal Structure Analysis; Institut für Anorganische Chemie der Universität, University of Göttingen: Göttingen, Germany, 1998.
25. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.
26. Clark, M.; Cramer, R. D., III; van Opdenbosch, N. J. Comput. Chem. 1989, 10, 982-1012.
27. Burkert, U.; Allinger, N. L. Molecular Mechanics; ACS Monograph 177; American Chemical Society: Washington, DC, 1982.