Progress toward the total synthesis of (±)-havellockate

Journal of Organic Chemistry

Volumn 75, Issue 19, 2010, Pages 6337-6346

  Beingessner, Rachel L ^a,b   Farand, Julie A ^a,c   Barriault, Louis ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^c MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON FRAMEWORK; DIELS-ALDER; DITERPENES; HYDRINDANE; INDIAN OCEAN; STEREOGENIC CENTERS; TOTAL SYNTHESIS;

CHEMICAL OPERATIONS; OLEFINS; STEREOCHEMISTRY;

SYNTHESIS (CHEMICAL);

DITERPENE; HAVELLOCKATE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CORAL; DIELS ALDER REACTION; NONHUMAN; SINULARIA GRANOSA; STEREOCHEMISTRY; SYNTHESIS;

ANIMALS; ANTHOZOA; DITERPENES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 77957144308     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101279z     Document Type: Article

References (34)

1. Faulkner, D. J. Nat. Prod. Rep. 2000, 17, 7 and references therein.
2. Faulkner, D. J. Nat. Prod. Rep. 1995, 2, 223
3. Anjaneyulu, A. S. R.; Venugopal, M. J. R. V.; Sarada, P.; Clardy, J.; Lobkovsky, E. Tetrahedron Lett. 1998, 39, 139
4. Roethle, P. A.; Trauner, D. Nat. Prod. Rep. 2008, 25, 298
5. Anjaneyulu, A. S. R.; Venugopal, M. J. R. V.; Sarada, P. Indian J. Chem. 2000, 39B, 530
6. For a previous synthetic study on havellockate, see: Mehta, G.; Senthil Kumaran, R. Tetrahedron Lett. 2001, 42, 8097
7. Ward, D. E.; Abaee, M. S. Org. Lett. 2000, 2, 3937
8. Ward, D. E.; Souweha, M. S. Org. Lett. 2005, 7, 3533
9. Barriault, L.; Thomas, J. D. O.; Clement, R. J. Org. Chem. 2003, 68, 2317
10. Barriault, L.; Ang, P. A. J.; Lavigne, R. M. A. Org. Lett. 2004, 6, 1317
11. Barriault, L.; Grisé, C. M.; Clément, R. Chem. Commun. 2008, 3004
12. For a review on tethers in cycloaddition, see
13. Shea, K. J.; Zandi, K. S.; Gauthier, D. R. Tetrahedron 1998, 54, 2289
14. For other examples of the use of temporary tethers in Diels-Alder reactions, see: Souweha, M. S.; Arab, A.; ApSimon, M.; Fallis, A. G. Org. Lett. 2007, 9, 615
15. Nicolaou, K. C.; Harrison, S. T. Angew. Chem., Int. Ed. 2006, 45, 3256
16. Zografos, A. L.; Yiotakis, A.; Georgiadis, D. Org. Lett. 2005, 7, 4515
17. Rath, J.-P.; Kinast, S.; Maier, M. E. Org. Lett. 2005, 7, 3089
18. Olsson, R.; Bertozzi, F.; Fredj, T. Org. Lett. 2000, 2, 1283
19. Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450
20. Curran, T. T.; Hay, D. A.; Koegel, C. P.; Evans, J. C. Tetrahedron 1997, 53, 1983
21. Johnson, C. R.; Adams, J. P.; Matthew, P. B.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 917
22. Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 919
23. Nakai, T.; Sugiura, M. Tetrahedron Lett. 1996, 37, 7991
24. Mikami, K.; Takahashi, K.; Nakai, T. Tetrahedron Lett. 1987, 28, 5879
25. Nordmann, F.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 4978
26. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011
27. Nicolaou, K. C.; Zhang, Y. L.; Baran, P. S. J. Am. Chem. Soc. 2000, 122, 7596
28. Nicolaou, K. C.; Montagnon, T.; Baran, P. S. Angew. Chem., Int. Ed. 2002, 41, 1386
29. Berkowitz, W. F.; Wilson, P. J. J. Org. Chem. 1991, 56, 3097
30. Jackman, L. M.; Webb, R. L.; Yick, H. C. J. Org. Chem. 1982, 47, 1824
31. We noticed that the yield of this elimination is highly dependent on the reaction scale. On a scale larger than 100 mg, the yield varies between 30 and 50%.
32. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100
33. Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347
34. Scarlato, G. R.; DeMattei, J. A.; Chong, L. S.; Ogawa, A. K.; Lin, M. R.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6139