Synthesis of (+/-) mappicine and mappicine ketone

Journal of Heterocyclic Chemistry

Volumn 40, Issue 4, 2003, Pages 601-605

  Henegar, Kevin E ^a   Baughman, Ted A ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; BENZALDEHYDE DERIVATIVE; CAMPTOTHECIN; KETONE; MAPPICINE; MAPPICINE KETONE; N TERT BUTYLOXYCARBONYL 2 AMINOBENZALDEHYDE; PYRIDINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; DEGRADATION; OXIDATION; POLYMERIZATION; SYNTHESIS;

EID: 0141507996     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570400407     Document Type: Article

References (31)

1. T. R. Govindachari, K. R. Ravindranath and N. Viswanathan, J. Chem. Soc. Perkin Trans. 1, 11, 1215 (1974).
2. T.-S. Wu, Y.-Y. Chan, L.-Y. Leu, C.-Y. Chem and C.-F. Chen, Phytochemistry, 42, 907 (1996).
3. [a] I. Pendrak, S. Barney, R. Wittrock, D. M. Lambert and W. D. Kingsbury, J. Org. Chem., 59, 2623 (1994);
4. [b] I. Pendrak, R. Wittrock, and W. D. Kingsbury, J. Org. Chem., 60, 2912-2915 (1995).
5. [a] T. Kametani, H. Takeda, H. Nemoto and K. Fukumoto, J. Chem. Soc. Perkin Trans. I, 18, 1825 (1975);
6. [b] D. L. Comins and J. K. Saha, J. Org. Chem., 61, 9623 (1996);
7. [c] H. Josien and D. P. Curran, Tetrahedron, 53, 8881 (1997);
8. [d] D. L. Boger and J. Hong, J. Am. Chem. Soc., 120, 1218 (1998);
9. [e] B. Das, P. Madhusudhan and A. Kashinatham, Bioorganic Med. Chem. Let., 8, 1403 (1998);
10. [f] J. S. Yadav, S. Sarkar and S. Chandrasekhar, Tetrahedron, 55, 5449 (1999);
11. [g] B. Das and P. Madhusudhan, Tetrahedron, 55, 7875 (1999);
12. [h] K. Mekouar, Y. Genisson, S. Leue, and A. E. Greene, J. Org. Chem., 65, 5212 (2000);
13. [i] M. Toyota, C. Komori and M. Ihara, J. Org. Chem., 65, 7110 (2000);
14. [j] L. Carles, K. Narkunan, S. Penlou, L. Rousset, D. Bouchu and M. A. Ciufolini, J. Org. Chem., 67, 4304 (2002).
15. Mappicine ketone: [a] W. D. Kingsbury, Tetrahedron Lett., 29, 6847 (1988);
16. [b] J. M. Fortunak, A. R. Mastrocola, M. Mellinger and J. L. Wood, Tetrahedron Lett., 35, 5763 (1994);
17. [c] B. Das and P. Madhusudhan, Syn. Comm., 30, 3321 (2000);
18. [d] B. Das, P. Madhusudhan and A. Kashinatham, Tetrahedron Lett., 39, 431 (1998).
19. Mappicine [a] B. Das, P. Madhusudhan and A. Kashinatham, Bioorganic Med. Chem. Let., 8, 1403 (1998);
20. [b] B. Das, P. Madhusudhan and B. Venkataiah, J. Indian Chem. Soc., 75, 662 (1998).
21. K. E. Henegar, S. W. Ashford, T. A. Baughman, J. C. Sih and R.-L. Gu, J. Org. Chem., 62, 6588 (1997).
22. [a] G. A. Olah, S. C. Narang, B. G. B. Gupta and R. Malhotra, J. Org. Chem., 44, 1247 (1979);
23. [b] M. E. Jung and M. A. Lyster J. Org. Chem., 42, 3761;
24. [c] T. Morita, Y. Okamoto and H. Sakurai, J. Chem. Soc. Chem. Comm., 874 (1978).
25. C.-C. Cheng and S.-J. Yan, in Organic Reactions, Vol 28, W. G. Dauben., ed, John Wiley and Sons, New York, NY, 1982, p. 37-201.
26. L. I. Smith and J. W. Opie, in Organic Syntheses Col. Vol III, E. C. Horning, ed, John Wiley and Sons, New York, NY, 1955, p. 56-58.
27. [a] W. Borsche, M. Wagner-Roemmich and J. Barthenheier, Liebigs Ann. Chem. 550, 160 (1942);
28. [b] W. Borsche and W. Ried, Liebigs Ann. Chem. 554, 269 (1943).
29. J. M. Muchowski and M. C. Venuti, J. Org. Chem., 45, 4798 (1980).
30. 3, see: [a] T. Akiyama, H. Shima and S. Ozaki, Tetrahedron Lett., 32, 5593 (1991);
31. [b] E. D. Moher, D. J. Rica and V. D. Tran, J. Am Chem. Soc., 114, 2764 (1992).