Novel terpenoids from the West Indian sea whip Pseudopterogorgia elisabethae (Bayer). Elisapterosins A and B: Rearranged diterpenes possessing an unprecedented cagelike framework

Journal of Organic Chemistry

Volumn 65, Issue 5, 2000, Pages 1390-1398

  Rodriguez, Abimael D ^a   Ramírez, Catherine ^b   Rodiiguez, Ileana I ^a   Barnes, Charles L ^b  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^b UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 EPI ELISABANOLIDE; ELISABETHIN D; ELISABETHIN D ACETATE; ELISAPTEROSIN A; ELISAPTEROSIN B; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ANIMAL TISSUE; ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; CORAL; DRUG ISOLATION; DRUG STRUCTURE; MOLECULAR MODEL; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ANIMALS; ANTITUBERCULAR AGENTS; BRIDGED COMPOUNDS; CNIDARIA; CRYSTALLOGRAPHY, X-RAY; DITERPENES; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; POLYCYCLIC COMPOUNDS; TUMOR CELLS, CULTURED; WEST INDIES;

EID: 0037601219     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9914869     Document Type: Article

References (31)

1. (a) Look, S. A.; Fenical, W.; Matsumoto, G. K; Clardy, J. J. Org. Chem. 1986, 51, 5140-5145.
2. (b) Roussis, V.; Wu, Z.; Fenical, W.; Strobel, S. A.; Van Duyne, G. D.; Clardy, J. J. Org. Chem. 1990, 55, 4916-4922.
3. Harvis, C. A.; Burch, M. T.; Fenical, W. Tetrahedron Lett. 1988, 29, 4361-4364.
4. Fenical, W. J. Nat. Prod. 1987, 50, 1001-1008.
5. (e) Wright, A. E.; Burres, N. S.; Schulte, G. K. Tetrahedron Lett. 1989, 30, 3491-3494.
6. (f) Bandurraga, M. M.; Fenical, W.; Donovan, S. F.; Clardy, J. J. Am. Chem. Soc. 1982, 104, 6463-6465.
7. (g) Rodriguez, A. D.; Shi, J.-G. J. Org. Chem. 1998, 63, 420-421.
8. (h) Look, S. A.; Burch, M. T.; Fenical, W.; Qi-tai, Z.; Clardy, J. J. Org. Chem. 1985, 50, 5741-5746.
9. Rodriguez, A. D.; Shi, J.-G.; Huang, S. D. J. Org. Chem. 1998, 63, 4425-4432.
10. j) Tinto, W. F.; Chan, W. R.; Reynolds, W. F.; McLean, S. Tetrahedron Lett. 1990,37,465-468.
11. (k) Chan, W. R.; Tinto, W. F.; Laydoo, R. S.; Machand, P. S.; Reynolds, W. F.; McLean, S. J. Org. Chem. 1991, 56, 1773-1776.
12. Tinto, W. F.; Lough, A. J.; Reynolds, W. F.; McLean, S. Tetrahedron Lett. 1991, 32, 4661-4664.
13. Tinto, W. F.; John, L.; Reynolds, W. F.; McLean, S. Tetrahedron 1991, 47, 8679-8686.
14. (n) Tinto, W. F.; Laydoo, R. S.; Miller, S. L.; Reynolds, W. F.; McLean, S. J. Nat. Prod. 1995,58,19751977.
15. (o) Rodriguez, A. D.; Soto, J. J. Chem. Pharm. Bull. 1996, 44, 91-94.
16. (p) Rodriguez, A. D.; Soto, J. J. Tetrahedron Lett. 1996, 37, 2687-2690.
17. (q) Rodriguez, A. D.; Soto, J. J. J. Org. Chem. 1996, 61, 4487-4490.
18. (r) Rodriguez, A. D.; Soto, J. J. J. Nat Prod. 1998,61,401404.
19. (s) Rodriguez, A. D.; Shi, J.-G.; Huang, S. D. J. Nat. Prod. 1999, 62. 1228-1237.
20. Rodriguez, A. D. Tetrahedron 1995, 51, 4571-4618 and references therein.
21. Rodriguez, A. D.; Gonzalez, E.; Huang, S. D. J. Org. Chem. 1998, 63, 7083-7091.
22. Rodriguez, A. D.; Ramirez, C.; Rodriguez, 1.1. Tetrahedron Lett. 1999, 40, 7627-7631.
23. Rodriguez, A. D.; Ramirez, C.; Rodriguez, 1.1. 7. Nat. Prod. 1999, 62, 997-999.
24. Rodriguez, A. D.; Ramirez, C.; Rodriguez, 1.1.; Gonzalez, E. Org. Lett. 1999, 1, 527-530.
25. We have also detected traces of pseudopterosins in our gorgonian specimen. The presence of these amphilectane-based diterpene glycosides is usually indicative of P. elisabethae and thus constitutes a useful chemotaxonomic marker.
26. The 'H NMR chemical shifts for these protons in benzene-c?6 were δ 1.26 (Me-20) and 1.54 (Me-13).
27. Jackman, L. M.; Sternhell, S. Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry; International Series in Organic Chemistry; Pergamon Press: Oxford, U.K., 1969; Vol. 10, Chapter 4-2, pp 280-304.
28. (12) We also found that treatment of elisapterosin A (6) (3.7 mg, 0.011 mmol) with lead tetraacetate (9 mg, 0.02 mmol) in dry benzene (4 mL) and pyridine (2 drops) afforded the desired Cig diketones 4 and 5 in a 1:1 ratio after refluxing for 22.5 h at 80 C as determined by TLC and GC-MS analyses.
29. Hudlicky, M. J. Org. Chem. 1980, 45, 5377.
30. Molecular Structure Corporation (1985,1992). TEXSAN. Crystal Structure Analysis Package; MSC, 3200 Research Forest Dr., The Woodlands, TX 77381.
31. Cromer, D. T.; Waber, J. T. International Tables for X-ray Crystallography; The Kynoch Press: Birmingham, U.K., 1974; Vol. IV, Tables 2.3.1 and 2.2A.