An improved synthesis of the tricyclic core of sarains by a 3-oxidopyridinium betaine cycloaddition

Heterocycles

Volumn 62, Issue , 2004, Pages 407-422

  Lee, Hyoung Ik ^a   Sung, Moo Je ^a   Lee, Hee Bong ^a   Cha, Jin Kun ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; BETAINE DERIVATIVE; PYRIDINIUM DERIVATIVE; SARAIN; TRICYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DIASTEREOISOMER; DRUG SYNTHESIS; HYDROGENATION; OXIDATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0346459975     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-s(p)29     Document Type: Article

References (31)

1. a) Part 3 in the series "Synthetic studies toward sarain A". Part 1. M. J. Sung, H. I. Lee, Y. Chong, and J. K. Cha, Org. Lett., 1999, 1, 2017;
2. Part 2. M. J. Sung, H. I. Lee, H. B. Lee, and J. K. Cha, J. Org. Chem., 2003, 68, 2205.
3. a) G. Cimino, C. A. Mattia, L. Mazzarella, R. Puliti, G. Scognamiglio, A. Spinella, and E. Trivellone, Tetrahedron, 1989, 45, 3863;
4. b) Y. Guo, A. Madaio, E. Trivellone, G. Scognamiglio, and G. Cimino, Tetrahedron, 1996, 52, 8341;
5. c) V. Caprioli, G. Cimino, A. De Guilio, A. Madaio, G. Scognamiglio, and E. Trivellone, Comp. Biochem. Physiol., 1992, 103B, 293.
6. a) L. Gil, A. Gateau-Olesker, C. Marazano, and B. C. Das, Tetrahedron Lett., 1995, 36, 707;
7. b) A. Kaiser, X. Billot, A. Gateau-Olesker, C. Marazano, and B. C. Das, J. Am. Chem. Soc., 1998, 120, 8026;
8. c) K. Jakubowicz, K. B. Abdeljelil, M. Herdemann, M.-T. Martin, A. Gateau-Olesker, A. A. Mourabit, C. Marazano, and B. C. Das, J. Org. Chem., 1999, 64, 7381. Cf.
9. d) J. E. Baldwin and R. C. Whitehead, Tetrahedron Lett., 1992, 33, 2059;
10. e) J. E. Baldwin, L. Bischoff, T. D. W. Claridge, F. A. Heupel, D. R. Spring, and R. C. Whitehead, Tetrahedron, 1997, 53, 2271.
11. a) J. Sisko and S. M. Weinreb, J. Org. Chem., 1991, 56, 3210;
12. b) J. Sisko, J. R. Henry, and S. M. Weinreb, J. Org. Chem., 1993, 58, 4945;
13. c) O. Irie, K. Samizu, J. R. Henry, and S. M. Weinreb, J. Org. Chem., 1999, 64, 587.
14. a) B. R. Henke, A. J. Kouklis, and C. H. Heathcock, J. Org. Chem., 1992, 57, 7056;
15. b) C. H. Heathcock, M. Clasby, D. A. Griffith, B. R. Henke, and M. J. Sharp, Synlett, 1995, 467;
16. c) D. J. Denhart, D. A. Griffith, and C. H. Heathcock, J. Org. Chem., 1998, 63, 9616;
17. d) C. M. Blazey and C. H. Heathcock, J. Org. Chem., 2002, 67, 298 and references therein.
18. a) R. Downham, F. W. Ng, and L. E. Overman, J. Org. Chem., 1998, 63, 8096;
19. b) S. Jaroch, R. T. Matsuoka, and L. E. Overman, Tetrahedron Lett., 1999, 40, 1273.
20. M. J. Sung, Ph. D. Dissertation, The University of Alabama, December 2001.
21. a) S.-j. Jin, J.-R. Choi, J. Oh, D. Lee, and J. K. Cha, J. Am. Chem. Soc., 1995, 117, 10914;
22. b) J. C. Lee, S.-j. Jin, and J. K. Cha, J. Org. Chem., 1998, 63, 2804;
23. c) J. K. Cha and J. Oh, Curr. Org. Chem., 1998, 2, 217.
24. a) N. Dennis, B. Ibrahim, and A. R. Katritzky, J. Chem. Soc., Perkin Trans. 1, 1976, 2307;
25. A. R. Katritzky, S. Rahimi-Rastgoo, G. J. Sabongi, and G. W. Fischer, J. Chem. Soc., Perkin Trans. 1, 1980, 362.
26. For reviews, see: c) N. Dennis, A. R. Katritzky, and Y. Takeuchi, Angew. Chem., Int. Ed. Engl., 1976, 15, 1;
27. d) A. R. Katritzky and N. Dennis, Chem. Rev., 1989, 89, 827.
28. No study has been undertaken to examine the reaction parameters that influence the product ratios of 7 to 8.
29. S. V. Ley, J. Norman, W. P. Griffith, and S. P. Marsden, Synthesis, 1994, 639.
30. M. F. Lipton, A. Basha, and S. M. Weinreb, 'Organic Syntheses,' Coll. Vol. VI, Wiley, New York, 1988, p. 492.
31. 1H COSY and difference NOE experiments.