Synthesis of the naturally occurring prenylated coumarins balsamiferone and cedrelopsin by domino reactions

Arkivoc

Volumn 2011, Issue 9, 2011, Pages 68-76

  Patre, Rupesh E ^a   Parameswaran, Perunninakulath S ^b   Tilvea, Santosh G ^a  

^a GOA UNIVERSITY   (India)

^b NATIONAL INSTITUTE OF OCEANOGRAPHY   (India)

Author keywords

Balsamiferone; Cedrelopsin; Claisen rearrangement; Cope rearrangement; Domino reaction; Wittig reaction

Indexed keywords

EID: 79955159608     PISSN: 1551-7012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0012.905     Document Type: Article

References (36)

1. (a) Murray, R. D. H. Nat. Prod. Rep. 1995, 12, 477.
2. (b) Estvez-Braun, A.; Gonzalez, A. G. Nat. Prod. Rep. 1997, 14, 465.
3. (c) Malikov, V. M.; Saidkhodzhaev, A. I. Khim. Prir. Soedin, 1998, 234, 250.
4. (a) Garazd, M. M.; Garazd, Y. L.; Khilya, V. P.; Khim. Prir. Soedin, 2003, 39, 47.
5. (b) Patil, A.D.; Freyer, A. J.; Eggleston, D. S.; Haltiwanger, R. C.; Bean, M. F.; Taylor, P. B.; Carranfer, M. J.; Breen, A. L.; Bartus, H. R.; Johnson, R. K.; Hertzberg, R. P.; Westley, J. W. J. Med. Chem. 1993, 36, 4131.
6. (c) Argotle-Ramos, R.; Ramirez-Avila, G.; Rodriquez- Gutierrez, M. D. C.; Qvilla-Munoz, M.; Lanz-Mendoz, H.; Rodriguez, M. H.; Gonzalez- Cartazar, M.; Alvarez, L. J. Nat. Prod. 2006, 69, 1442.
7. (d) Verotta, L.; Lovaglio, E.; Vidari, G.; Finzi, P. V.; Neri, M. G.; Raimondi, A.; Parapini, S.; Taramelli, D.; Riva, A.; Bombardelli, E. Phytochemistry 2004, 65, 2867.
8. (e) Guilet, D.; Helesbeux, J. -J.; Seraphin, D.; Serenet, T.; Richomme, P.; Bruneton, J. J. Nat. Prod. 2001, 64, 563.
9. (f) O'Kennedy, R.; Thornes, R. D. Coumarins: Biology, Applications and Mode of Action, Wiley & Sons, Chichester, 1997.
10. Murray, R. D. Natural Coumarin: Occurrence, Chemistry and Biochemistry Wiley: New York, 1982.
11. Reisch, J.; Szendrei, K.; Minker, K. E.; Novak, I. Experientia 1968, 24, 992.
12. Burke, B. A.; Parkins, H. Phytochemistry 1979, 18, 1073.
13. (a) Prakash, D.; Lakshmi, V.; Raj, K.. Kapil, R. S. Fitoterapia 1989, 60, 347.
14. (b) Ito, C. Itoigawa, M.; Ju-ichi, M.; Sakamoto, N.; Tokuda, H.; Nishino, H.; Furukawa, H. Plant Medica 2005, 71, 84.
15. Eshiett, T; Taylor, D. A. H. J. Chem. Soc. 1968, 481.
16. Tietze, L. F. Chem. Rev. 1996, 96, 115.
17. (a) Posner, G. H. Chem. Rev. 1986, I, 831.
18. (b) Jasperse, C. P.; Curran, D. P; Fevig ,T. L. Chem. Rev. 1991, 91, 1237.
19. (c) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P.G. Angew. Chem. Int. Ed. 2006, 45, 7134.
20. (d) Pelliser, H. Tetrahedron 2006, 4, 2076.
21. (e) Kirsch, S.F. Synthesis 2008, 20, 3183.
22. (f) Tietze, L. F.; Beifuss, U. Angew. Chem. Int. Ed. 1993, 32, 131.
23. (g) Tietze, L. F.; Lieb, M. Curr. Opin. Chem. Biol. 1998, 2, 363.
24. (h) Tietze L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304.
25. (i) Tietze, L. F.; Brasche, G.; Gericke, G. Domino Reactions in Organic Synthesis, Wiley-VCH:Weinheim, 2006.
26. (j) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195.
27. (k) Ho, T. L. Tandem Reactions in Organic Synthesis, Wiely Interscience, New York, 1997.
28. (l) Taylor, R. J. K.; Reid, M.; Foot, M. J.; Raw, S. S. Acc Chem Res, 2005, 38, 851.
29. Patre, R. E.; Gawas, S.; Parameswaran, P. S.; Tilve, S. G. Tetrahedron Lett. 2009, 50, 6488.
30. Cairns, N.; Harwood, L. M.; Astle, D. P. J. Chem. Soc., Perkin Trans 1 1994, 3101.
31. (a) Sharma, R. B.; Swarrop, D.; Kapil, R. S. Indian J. Chem. 1983, 22B, 408.
32. (b) Sharma, R. B.; Swarrop, D.; Kapil, R. S. Indian J. Chem. 1982, 22B, 105.
33. Mali, R. S.; Joshi, P. P.; Sandhu, P. K.; Manekar-Tilve, A. J. Chem. Soc. Perkin. Trans. 1 2002, 371.
34. Shen, Y. H.; Li, S. H; Han, Q. B.; Sun, H. D. J. Asian. Nat. Prod. Res. 2006, 8, 345.
35. Mali, R. S.; Manekar, A. R.; Tilve, S. G. Org. Prep. Proced. Int. 1992, 24, 52.
36. Anet, F. A.; Hughes, G. K.; Ritchie, E. Austral. J. Sci. Res. 1949, A2, 608.