Correction of the structure of a new sesquiterpene from Cistus creticus ssp. creticus

Journal of Natural Products

Volumn 67, Issue 12, 2004, Pages 1996-2001

  Hatzellis, Konstantinos ^a   Pagona, Georgia ^a   Spyros, Apostolos ^a   Demetzos, Costas ^b   Katerinopoulos, Haralambos E ^a  

^a UNIVERSITY OF CRETE   (Greece)

^b UNIVERSITY OF ATHENS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

1,1,4A,6 TETRAMETHYL 5 METHYLENE 1,2,3,4,4ALPHA,5,8,8ALPHA OCTAHYDRONAPHTHALENE; 6 ISOPROPENYL 4,4A DIMETHYL 1,2,3,4,4A,5,6,7 OCTAHYDRONAPHTALENE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CIS ISOMER; CISTUS; DRUG SYNTHESIS; ISOMERISM; SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; TRANS ISOMER;

CATALYSIS; CISTUS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; NAPHTHALENES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANTS, MEDICINAL; SESQUITERPENES; STEREOISOMERISM;

CISTUS; CISTUS INCANUS SUBSP. CRETICUS;

EID: 11844266564     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0498556     Document Type: Article

References (39)

1. Demetzos, C.; Mitaku, S.; Loukis, A.; Harvala, C.; Gaily, A. J. Essent. Oil Res. 1994, 61, 37-41.
2. Demetzos, C.; Katerinopoulos, H.; Kouvarakis, A.; Stratigakis, N.; Loukis, A.; Ekonomakis, C.; Spiliotis, V.; Tsaknis, J. Planta Med. 1997, 63, 477-479.
3. Demetzos, C.; Loukis, A.; Spiliotis, V.; Zoakis, N.; Stratigakis, N.; Katerinopoulos, H. E. J. Essent. Oil. Res. 1995, 7, 407-410.
4. Demetzos, C. Phytochemical Analysis of Cistus creticus. Isolation, Synthesis, and Structure Elucidation of a New Flavonoid Glycoside from Kalanhoe prolifera R. Hamet. Ph.D. Thesis, University of Athens, Greece, 1990.
5. Chinou, I.; Demetzos, C.; Harvala, C.; Eoussakis, C.; Verbist, J. F. Planta Med. 1994, 60, 34-6.
6. Demetzos, C.; Stahl, B.; Anastassaki, T.; Gazouli, M.; Tzouvelekis, L. S.; Rallis, M. Planta Med. 1998, 65, 76-78.
7. Polovinka, M. P.; Korchagtna, D. V.; Gatilov, Y. V.; Bagrianskaya, I. Y.; Barkhash, V. A.; Perutskii, V. B.; Ungur, N. D.; Vlad, P. V.; Shcherbukhin, V. V.; Zefirov, N. S. J. Org. Chem. 1994, 59, 1509-1517.
8. Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chanboun, R. Tetrahedron 1998, 54, 5635-5650.
9. Akita, H.; Nozawa, M.; Mitsuda, A.; Ohsawa, H. Tetrahedron Asymm. 2000, 11, 1375-1388.
10. Corey, E. J.; Ohno, M.; Mitra, B. B.; Vatakencherry, P. A. J. Am. Chem. Soc. 1964, 86, 478-485.
11. Ling, T.; Kramer, B. A.; Palladino, M. A.; Theodorakis, E. A. Org. Lett. 2000, 2, 2073-2076.
12. Kametani, T.; Suzuki, K.; Nemoto, H. J. Org. Chem. 1980, 45, 2204-2207.
13. Hagiwara, H.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1991, 1803-1807.
14. Ciceri, P.; Demnitz, F. W. J. Tetrahedron Lett. 1997, 38, 389-390.
15. Woodward, B. B.; Patchett, A. A.; Barton, D. H. R.; Ives, D. A. J.; Kelly, R. B. J. Am. Chem. Soc. 1954, 76, 2852-2853.
16. Experimental conditions used were similar to those reported by: King J.; Quale, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221-5224.
17. Gesson, J.-P.; Jacquesy, J.-C.; Renoux, B. Tetrahedron Lett. 1986, 27, 4461-4464.
18. Gesson, J.-P.; Jacquesy, J.-C.; Eenoux, B. Tetrahedron 1989, 45, 5853-5866.
19. Tokoroyama, T.; Tsukamoto, M.; Asada, T.; Iio, H. Tetrahedron Lett. 1987, 28, 6645-6648.
20. Anderson, J. C.; Pearson, D. J. Chem. Soc., Perkin Trans. 1 1998, 2023-2029.
21. Park, K.; Scott, W. J.; Wiemer, D. F. J. Org. Chern. 1994, 59, 6313-6317.
22. (a) Sondheimer, F.; Elad, D. J. Am. Chem. Soc. 1957, 79, 5542-5546.
23. Spectral data are indicative of the proposed stereochemistry as reported by: (b) Cheung, W. S.; Wong, H. N. C. Tetrahedron 1999, 55, 11001-11016.
24. Snitman, D. L.; Tsai, M.-Y.; Watt, D. S.; Edwards, C. L. J. Org. Chem. 1979, 44, 2838-2842.
25. Experimental conditions similar to those reported by: Grieco, P. A.; Yokoyama, Y.; Withers, G. P.; Okuniewicz, F. J.; Wang, C. L. J. J. Org. Chem. 1978, 43, 4178-4182.
26. Failure of Wittig-type reactions is propably due to steric hindrance and has been reported in similarly hindered systems: McMurry, J. E.; Choy, W.; Tetrahedron Lett. 1980, 21, 2477-2480.
27. Abad, A.; Agullo, C.; Cunat, A. C.; Perni, R. H. Chem. Commun. 1999, 427-428.
28. Corey, E. J.; Kang, J.; Kyler, K. Tetrahedron Lett. 1985, 26, 555-558.
29. Toshima, H.; Oikawa, H.; Toyomasu, T.; Sassa, T. Tetrahedron 2000, 56, 8443-8450.
30. Almstead, J. K.; Demuth, T. P., Jr.; Ledoussal, B. Tetrahedron Asymmetry 1998, 9, 3179-3183.
31. Smith, A. B., III; Jerris, P. J. J. Org. Chem. 1982, 47, 1845-1855.
32. Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392-6394.
33. Petasis, N. A.; Lu, S. H. Tetrahedron Lett. 1995, 36, 2393-2396.
34. Burgess, E. M.; Penton, H. R.; Taylor, E. A. J. Org. Chem. 1973, 38, 26-31.
35. Goldsmith, D. J.; Kezar, H. S. Tetrahedron Lett. 1980, 21, 3543-3546.
36. Adams, R. P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy; Allure Publishing Co.: Carol Stream, IL, 1995; p 282.
37. Calculations were performed with the GAUSSIAN 94 program package. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari; K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision D.4; Gaussian, Inc.: Pittsburgh, PA, 1995.
38. Abell, A. D.; Massy-Westropp, R. A. Aust. J. Chem. 1985, 38, 1263-1269.
39. Itokawa, H.; Morita, H.; Watanabe, K.; Mihashi, S.; Itaka, Y. Chem. Pharm. Bull. 1985, 33, 1148-1153.