Unified synthesis of caged Garcinia natural products based on a site-selective Claisen/Diels-Alder/Claisen rearrangement

Proceedings of the National Academy of Sciences of the United States of America

Volumn 101, Issue 33, 2004, Pages 12030-12035

  Tisdale, Eric J ^a   Slobodov, Irina ^a   Theodorakis, Emmanuel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DESOXYGAUDICHAUDIONE A; DESOXYMORELLIN; FORBESIONE; GAMBOGIN; NATURAL PRODUCT; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CLAISEN REARRANGEMENT; CYCLIZATION; DIELS ALDER REACTION; GARCINIA; MOLECULAR STABILITY; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

BIOLOGICAL PRODUCTS; BRIDGED COMPOUNDS; CHEMISTRY, ORGANIC; GARCINIA; HETEROCYCLIC COMPOUNDS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; XANTHENES; XANTHONES;

BETULACEAE; GARCINIA;

EID: 4344608504     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0401932101     Document Type: Article

References (35)

1. Ollis, W. D., Redman, B. T., Sutherland, I. O. & Jewers, K. (1969) J. Chem. Soc. Chem. Commun., 879-880.
2. Kumar, P. & Baslas, R. K. (1980) Herba Hung. 19, 81-91.
3. Thoison, O., Fahy, J., Dumontet, V., Chiaroni, A., Riche, C., Tri, M. V. & Sevenet, T. (2000) J. Nat. Prod. 63, 441-446.
4. Gruenwald, J., Brendler, T. & Jaenicke, C., eds. (2000) PDR for Herbal Medicines (Medical Economics, Montvale, NJ), 2nd Ed., pp. 325-326.
5. Kartha, G., Ramachandran, G. N., Bhat, H. B., Nair, P. M., Raghavan, V. K. V. & Venkataraman, K. (1963) Tetrahedron Lett. 4, 459-462.
6. Leong, Y.-W., Harrison, L. J., Bennett, G. J. & Tan, H. T.-W. (1996) J. Chem. Res. Synop., 392-393.
7. Venkataraman, K. (1974) Proc. Indian Natl. Sci. Acad. Part A Phys. Sci. 39, 365-381.
8. Karanjgaonkar, C. G., Nair, P. M. & Venkataraman, K. (1966) Tetrahedron Lett. 7, 687-691.
9. Ollis, W. D., Ramsay, M. V. J., Sutherland, I. O. & Mongkolsuk, S. (1965) Tetrahedron 21, 1453-1470.
10. Asano, J., Chiba, K., Tada, M. & Yoshii, T. (1996) Phytochemistry 41, 815-820.
11. Cao, S.-G., Wu, X.-H., Sim, K.-Y., Tan, B. K. H., Pereira, J. T., Wong, W. H., Hew, N. F. & Goh, S. H. (1998) Tetrahedron Lett. 39, 3353-3356.
12. Ahmad, S. A., Rigby, W. & Taylor, R. B. (1966) J. Chem. Soc. C, 772-779.
13. Zhang, H.-Z., Kasibhatla, S., Wang, Y., Herich, J., Guastella, J., Tseng, B., Drewe, J. & Cai, S.-X. (2004) Bioorg. Med. Chem. 12, 309-317.
14. Wu, X., Cao, S., Goh, S., Hsu, A. & Tan, B. K. H. (2002) Planta Med. 68, 198-203.
15. Quillinan, A. J. & Scheinmann, F. (1971) J. Chem. Soc. Chem. Commun., 966-967.
16. Nicolaou, K. C. & Li, J. (2001) Angew. Chem. Int. Ed. Engl. 40, 4264-4268.
17. Tisdale, E. J., Chowdhury, C., Vong, B. G., Li, H. & Theodorakis, E. A. (2002) Org. Lett. 4, 909-912.
18. Tisdale, E. J., Slobodov, I. & Theodorakis E. A. (2003) Org. Biomol. Chem. 1, 4418-4422.
19. Ishiguro, K., Nagareya, N., Suitani, A. & Fukumoto, H. (1997) Phytochemistry 44, 1065-1066.
20. Chung, M.-I., Weng, J.-R., Lai, M.-H., Yen, M.-H. & Lin, C.-N. (1999) J. Nat. Prod. 62, 1033-1035.
21. Burling, E. D., Jefferson, A. & Scheinmann, F. (1965) Tetrahedron 21, 2653-2669.
22. Pettus, T. R. R. & Hoarau, C. (2003) Synlett, 127-137.
23. Perrin, R., Muyard, F., Bevalot, F., Tillequin, F. & Vaquette, J. (2000) J. Nat. Prod. 63, 245-247.
24. Hlubucek, J., Ritchie, E. & Taylor, W. C. (1971) Aust. J. Chem. 24, 2355-2363.
25. Tisdale, E. J., Kochman, D. A. & Theodorakis, E. A. (2003) Tetrahedron Lett. 44, 3281-3284.
26. Tisdale, E. J., Vong, B. G., Li, H., Kim, S. H., Chowdhury, C. & Theodorakis, E. A. (2003) Tetrahedron 59, 6873-6887.
27. Coates, R. M., Rogers, B. D., Hobbs, S. J., Peck, D. R. & Curran, D. P. (1987) J. Am. Chem. Soc. 109, 1160-1170.
28. Gajewski, J. J., Jurayi, J., Kimbrough, D. R., Gande, M. E., Ganem, B. & Carpenter, B. K. (1987) J. Am. Chem. Soc. 109, 1170-1186.
29. Kupczyk-Subotkowska, L., Saunders, W. H., Jr., & Shine, H. J. (1988) J. Am. Chem. Soc. 110, 7153-7159.
30. Gajewski, J. J. (1997) Acc. Chem. Res. 30, 219-225.
31. Wipf, P. & Rodriguez, S. (2002) Adv. Synth. Catal. 344, 434-440.
32. Nicolaou, K. C., Sasmal, P. K., Xu, H., Namoto, K. & Ritzen, A. (2003) Angew. Chem. Int. Ed. Engl. 42, 4225-4229.
33. Tisdale, E. J., Li, H., Vong, B. G., Kim, S. H. & Theodorakis, E. A. (2003) Org. Lett. 5, 1491-1494.
34. Murray, R. D. H., Sutcliffe, M. & Hasegawa, M. (1975) Tetrahedron 31, 2966-2972.
35. Pettus, T. R., Inoue, M., Chen, X.-T. & Danishefsky, S. J. (2000) J. Am. Chem. Soc. 122, 6160-6168.