Biosynthesis of baccharis oxide, a triterpene with a 3, 10-oxide bridge in the A-ring

Organic Letters

Volumn 10, Issue 21, 2008, Pages 5071-5074

  Shibuya, Masaaki ^a   Sagara, Aya ^a   Saitoh, Ai ^a   Kushiro, Tetsuo ^a   Ebizuka, Yutaka ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BACCHARIS OXIDE; EPOXIDE; TRITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; METABOLISM; MOLECULAR GENETICS; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY;

CYCLIZATION; EPOXY COMPOUNDS; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY, AMINO ACID; TRITERPENES;

EID: 58149149531     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802072y     Document Type: Article

References (29)

1. (a) Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890-1904,
2. (b) Eschenmoser, A.; Arigoni, D. Helv. Chim. Acta 2005, 88, 3011-3050.
3. Review: Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189-2206.
4. Review: Phillips, D. R.; Rasbery, J. M.; Bartel, B.; Matsuda, S. P. T. Curr. Opin, Plant Biol. 2006, 9, 305-314.
5. Xiong, Q.; Wilson, W. K.; Matsuda, S. P. T. Angew. Chem., Int. Ed. 2006, 45, 1285-1288,
6. Shibuya, M.; Xiang, T.; Katsube, Y.; Otsuka, M.; Zhang, H.; Ebizuka, Y. J.Am. Chem. Soc. 2007, 129, 1450-1455.
7. Roman, L. U.; Guerra-Ramirez, D.; Moran, G.; Martinez, I.; Heraandez, J. D.; Cerda-Garcia-Rojas, C. M.; Torres-Valencia, J. M.; Joseph-Nathan, P. Org. Lett. 2004, 6, 173-176.
8. Ibrahim, N. A.; El-Gengaihi, S.; Motawe, H.; Riad, S. A. Eur. Food Res. Technol. 2007, 224, 483-488.
9. Morita, M.; Shibuya, M.; Kushiro, M.; Masuda, K.; Ebizuka, Y. Eur. J. Biochem. 2000, 267, 3453-3460.
10. Kushiro. T.; Shibuya, M.; Ebizuka, Y. Eur. J. Biochem. 1998, 256, 238-244.
11. Nurnberg, V.; Fujiwara, F. Y.; Marsaioli, A. J. Magn. Reson. Chem. 1998, 36, 766-768.
12. Anthonse, T.; Bruun, T.; Hemmer, E.; Holme, D.; Lamvik, A.; Sunde, E.; Sorensen, N. A. Acta Chem. Scand. 1970, 24, 2479-2479.
13. (a) Mo, F.; Anthonse, T.; Bruun, T. Acta Chem. Scand. 1972, 26, 1287-1287.
14. (b) Mo, F. Acta Crystallogr. Sect. B: Struct. Sci. 1973, 29, 1796-1807, B.
15. Missima, F.; da Silva, A. A.; Nunes, G. A.; Bueno, P. C. P.; de Sousa, J. P. B.; Bastos, J. K.; Sforcin, J. M. J. Pharm. Pharmacol. 2007, 59, 463-468.
16. da Silva, A. A.; Bueno, P. C. P.; Gregorio, L. E.; e Silva, M. L. A.; Albuquerque, S.; Bastos, J. K. J. Pharm. Pharmacol. 2004, 56, 1195-1199.
17. Review: Xu, R.; Fazio, G. C.; Matsuda, S. P. T. Phytochemistry 2004, 65, 261-291.
18. (a) Kimura, K.; Hashimoto, Y.; Agata, I. Chem. Pharm. Bull. 1960, 8, 1145-1146.
19. (b) Arthur, H. R.; Hui, W. H. J. Chem. Soc. 1961, 551-551.
20. (c) Constantine, G. H., Jr; Block, J. H. Phytochemistry 1970, 9, 1659-1689.
21. (d) White, J. D.; Fayos, J.; Clardy, J. J. Chem. Soc. Chem. Comn. 1973, 357-358.
22. (e) Mo, F. Acta Crystal. Sec. B Structural Sci. 1977, 33, 641-649.
23. Akihisa, T.; Kimura, Y.; Tamura, T. Phytochemistry 1994, 37, 1413-1415.
24. Abe, I.; Prestwich, G. D. Lipids 1995, 30, 231-234.
25. (a) Hart, E. A.; Hua, L.; Darr, L. B.; Wilson, W. K.; Pang, J. H.; Matsuda, S. P. T, J. Am. Chem. Soc. 1999, 121, 9887-9888.
26. (b) Matsuda, S. P. T.; Darr, L. B.; Hart, E. A.; Herrera, J. B. R.; McCann, K. E.; Meyer. M. M.; Pang, J. H.; Schepmann, H. G. Org. Lett. 2000, 2, 2261-2263.
27. Kolesnikova, M. D.; Wilson, W. K.; Lynch, D. A.; Obermeyer. A. C.; Matsuda, S. P. T. Org. Lett. 2007, 9, 5223-5226.
28. Takahashi, T.; Moriyama, Y.; Tanahashi, Y.; Ourisson, G. Tetrahedron Lett. 1967, 31, 2991-2991.
29. Jefferies, P. R. J. Chem. Soc. 1954, 473-474.