Synthesis of β-boswellic acid analogues with a carboxyl group at c-17 isolated from the bark of Schefflera octophylla

Journal of Organic Chemistry

Volumn 65, Issue 19, 2000, Pages 6278-6282

  Bore, Lothar ^a,b   Honda, Tadashi ^a   Gribble, Gordon W ^a  

^a Dartmouth College   (United States)

^b CIBA GEIGY LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BOSWELLIC ACID; CARBOXYL GROUP; PALLADIUM COMPLEX;

COMPLEX FORMATION; DEACETYLATION; DERIVATIZATION; DRUG ISOLATION; DRUG SYNTHESIS; ENZYME ACTIVITY; MACROPHAGE ACTIVATION; NOTE; STRUCTURE ANALYSIS;

CHROMATOGRAPHY, THIN LAYER; PLANT EPIDERMIS; PLANTS, MEDICINAL; SUPPORT, NON-U.S. GOV'T; TRITERPENES;

EID: 0034703315     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0008688     Document Type: Note

References (28)

1. (a) Simmet, T.; Ammon, H. P. T. German Patent, DE 4445728 A1, 1996; Chem. Abstr. 1996, 125, 67823.
2. (a) Simmet, T.; Ammon, H. P. T. German Patent, DE 4445728 A1, 1996; Chem. Abstr. 1996, 125, 67823.
3. (b) Safayhi, H.; Rail, B.; Sailer E. R.; Ammon, H. P. T. J. Pharmacol. Exp. Ther. 1997, 281, 460.
4. (c) Knaus, U.; Wagner, H. Phytomedicine 1996, 3, 77.
5. (d) Safayhi, H.; Sailer, E. R.; Ammon, H. P. T. Phytomedicine 1996, 3, 71.
6. (e) Sailer, E. R.; Hoernlein, R. F.; Subramanian, L. R.; Ammon, H. P. T.; Safayhi, H. Arch. Pharm. (Weinheim, Ger.) 1996, 329, 54.
7. (a) Honda, T.; Finlay, H. J.; Gribble, G. W.; Suh, N.; Sporn, M. B. Bioorg. Med. Chem. Lett. 1997, 7, 1623.
8. (b) Finlay, H. J.; Honda, T.; Gribble, G. W.; Danielpour, D.; Benoit, N. E.; Suh, N.; Williams, C.; Sporn, M. B. Bioorg. Med. Chem. Lett. 1997, 7, 1769.
9. (c) Suh, N.; Honda, T.; Finlay, H. J.; Barchowsky, A.; Williams, C.; Benoit, N. E.; Xie, Q.; Nathan, C.; Gribble, G. W.; Sporn, M. B. Cancer Res. 1998, 58, 717.
10. (d) Honda, T.; Rounds, B. V.; Gribble, G. W.; Suh, N.; Wang, Y.; Sporn, M. B. Bioorg. Med. Chem. Lett. 1998, 8, 2711.
11. (e) Suh, N.; Wang, Y.; Honda, T.; Gribble, G. W.; Dmitrovsky, E.; Hickey, W. F.; Maue, R. A.; Place, A. E.; Porter D. M.; Spinella, M. J.; Williams, C. R.; Wu, G.; Dannenberg, A. J.; Flanders, K. C.; Letterio, J. J.; Mangelsdorf, D. J.; Nathan, C. F.; Nguyen, L.; Porter, W. W.; Ren, R. F.; Roberts, A. B.; Roche, N. S.; Subbaramaiah, K.; Sporn, M. B. Cancer Res. 1999, 59, 336.
12. (f) Honda, T.; Rounds, B. V.; Bore, L.; Favaloro, F. G., Jr.; Gribble, G. W.; Suh, N.; Wang, Y.; Sporn, M. B. Bioorg. Med. Chem. Lett. 1999, 9, 3429.
13. (g) Honda, T.; Gribble, G. W.; Suh, N.; Finlay, H. J.; Rounds, B. V.; Bore, L.; Favaloro, F. G., Jr.; Wang, Y.; Sporn, M. B. J. Med. Chem. 2000, 43, 1866.
14. Sung, T. V.; Lavaud, C.; Porzel, A.; Steglich, W.; Adam, G. Phytochemistry 1992, 31, 227.
15. (a) Baldwin, J. E.; Jones, R. H.; Najera, C.; Yus, M. Tetrahedron 1985, 41, 699.
16. (b) Carr, K.; Saxton, H. M.; Sutherland, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 1599.
17. (c) Peakman, T. M.; Lo ten Haven, H.; Rullkötter, J.; Tetrahedron 1991, 47, 3779.
18. Yasue, M.; Sakakibara, J.; Kaiya, T. J. Pharm. Soc. Jpn. (Yakugaku Zasshi) 1973, 93, 296, and references therein.
19. Triterpene acid corresponding to this methyl ester 15 is a naturally occurring triterpene isolated from twigs and leaves of Cussonia natalensis: Fourie, T. G.; Matthee, E.; Snyckers, F. O. Phytochemistry 1989, 28, 2851. This conversion of ursolic acid (5) into 15 is also the first synthesis of this natural product.
20. Kuwada, S.; Matsukawa, T. J. Pharm. Soc. Jpn. (Yakugaku Zasshi) 1933, 53, 593.
21. Huneck, S.; Snatzke, G. Chem. Ber. 1965, 98, 120.
22. 10 does not give methyl 3α-hydroxyurs-12-en-28-oate (methyl 3-epi-ursolate) from methyl 3β-hydroxyurs-12-en-28-oate (methyl ursolate) due to steric hindrance of the C-3 β-hydroxyl group (Honda, T. Unpublished data), we excluded this reaction from our synthetic route.
23. (a) Mitsunobu, O. Synthesis 1981, 1.
24. (b) Hughes, D. L. In Organic Reactions, Vol. 42; Paquette, L. A. et al., Eds.; John Wiley & Sons: New York, 1992; pp 335-656.
25. Braish, T. F.; Fuchs, P. L. Synth. Commum. 1986, 16, 111.
26. Carlsen, P. J.; Katsuki, T.; Martin, V. S.; Sharpless K. B. J. Org. Chem. 1981, 46, 3936.
27. Newton, R. F.; Reynolds, D. P.; Finch, M. A. W.; Kelly, D. R.; Roberts, S. M. Tetrahedron Lett. 1979, 3981.
28. 3 we could not compare our synthetic analogues with the natural products directly.