Pd-catalyzed carbonylative lactamization: A novel synthetic approach to FR900482

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1745-1748

  Trost, Barry M ^a   Ameriks, Michael K ^a,b  

^a STANFORD UNIVERSITY   (United States)

^b JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DINITRO 4 TOLUIC ACID; 4 FORMYL 6,9 DIHYDROXY 14 OXA 1,11 DIAZATETRACYCLO[7.4.1.0 2,7 0 10,12]TETRADECA 2,4,6 TRIEN 8 YLMETHYLCARBAMATE; ACETALDEHYDE; ACID; CARBONYL DERIVATIVE; LACTAM; METHYLEPHEDRINE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; POLYMERIZATION; STOICHIOMETRY;

CATALYSIS; CYCLIZATION; ISOMERISM; LACTAMS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXAZINES; PALLADIUM;

EID: 2942598446     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049583y     Document Type: Article

References (32)

1. Denny, W. A. In Cancer Chemotherapeutic Agents; Foye, W. A., Ed.: American Chemical Society: Washington, DC, 1995; pp 491-493.
2. Becherbauer, L.; Tepe, J. J.; Eastman, R. A.; Mixter, P. F.; Williams, R. M.; Reeves, R. Chem. Biol. 2002, 9, 427.
3. Uchida, I.; Shigehiro, T.; Hiroshi, K.; Sumio, K.; Hashimoto, M.; Tada, T.; Shigetaka, K.; Morimoto, Y. J. Am. Chem. Soc. 1987, 709, 4108.
4. Williams, R. M.; Ducept, P. Biochemistry 2003, 42, 14696 and references therein.
5. Terano, H.; Takase, S.; Hosoda, J.; Kohsaka, M. J. Antibiot. 1989, 42, 145.
6. For total syntheses of FR900482, see: (a) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (c) Kato, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10253. (d) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683. (e) Suzuki, M.; Kambe, M.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686.
7. For total syntheses of FR900482, see: (a) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (c) Kato, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10253. (d) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683. (e) Suzuki, M.; Kambe, M.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686.
8. For total syntheses of FR900482, see: (a) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (c) Kato, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10253. (d) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683. (e) Suzuki, M.; Kambe, M.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686.
9. For total syntheses of FR900482, see: (a) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (c) Kato, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10253. (d) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683. (e) Suzuki, M.; Kambe, M.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686.
10. For total syntheses of FR900482, see: (a) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722. (c) Kato, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10253. (d) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683. (e) Suzuki, M.; Kambe, M.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686.
11. For formal syntheses of FR900482, see: (f) Fellows, I. M.; Kaelin. D. E., Jr.; Martin, S. F. J. Am. Chem. Soc. 2000, 122, 10781. (g) Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130.
12. For formal syntheses of FR900482, see: (f) Fellows, I. M.; Kaelin. D. E., Jr.; Martin, S. F. J. Am. Chem. Soc. 2000, 122, 10781. (g) Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130.
13. For a total synthesis of FR66979, see: (h) Ducray, R.; Ciufolini, M. A.; Angew. Chem., Int. Ed. 2002, 41, 4688.
14. For reviews of mitomycin syntheses, see: (a) Kasai, M.; Kono, M. Synlett 1992, 778. (b) Remers, W. A.; Iynegar, B. S. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: New York, 1990; pp 415-445.
15. For reviews of mitomycin syntheses, see: (a) Kasai, M.; Kono, M. Synlett 1992, 778. (b) Remers, W. A.; Iynegar, B. S. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: New York, 1990; pp 415-445.
16. For synthetic routes to FR900482 utlizing benzazocines, see ref 6 as well as: (c) Ciufolini, M. A.; Chen, M.; Lovett, D. P.; Deaton, M. V. Tetrahedron Lett. 1997, 38, 4355. (d) Greshock, T. J.; Funk. R. L. J. Am. Chem. Soc. 2002, 124, 754. (e) Papaioannou, N.; Evans, C. A.; Blank, J. T.; Miller, S. J. Org. Lett. 2001, 3, 2879. (f) Yasuda, N.; Williams, R. M. Tetrahedron Lett. 1989, 30, 3397.
17. For synthetic routes to FR900482 utlizing benzazocines, see ref 6 as well as: (c) Ciufolini, M. A.; Chen, M.; Lovett, D. P.; Deaton, M. V. Tetrahedron Lett. 1997, 38, 4355. (d) Greshock, T. J.; Funk. R. L. J. Am. Chem. Soc. 2002, 124, 754. (e) Papaioannou, N.; Evans, C. A.; Blank, J. T.; Miller, S. J. Org. Lett. 2001, 3, 2879. (f) Yasuda, N.; Williams, R. M. Tetrahedron Lett. 1989, 30, 3397.
18. For synthetic routes to FR900482 utlizing benzazocines, see ref 6 as well as: (c) Ciufolini, M. A.; Chen, M.; Lovett, D. P.; Deaton, M. V. Tetrahedron Lett. 1997, 38, 4355. (d) Greshock, T. J.; Funk. R. L. J. Am. Chem. Soc. 2002, 124, 754. (e) Papaioannou, N.; Evans, C. A.; Blank, J. T.; Miller, S. J. Org. Lett. 2001, 3, 2879. (f) Yasuda, N.; Williams, R. M. Tetrahedron Lett. 1989, 30, 3397.
19. For synthetic routes to FR900482 utlizing benzazocines, see ref 6 as well as: (c) Ciufolini, M. A.; Chen, M.; Lovett, D. P.; Deaton, M. V. Tetrahedron Lett. 1997, 38, 4355. (d) Greshock, T. J.; Funk. R. L. J. Am. Chem. Soc. 2002, 124, 754. (e) Papaioannou, N.; Evans, C. A.; Blank, J. T.; Miller, S. J. Org. Lett. 2001, 3, 2879. (f) Yasuda, N.; Williams, R. M. Tetrahedron Lett. 1989, 30, 3397.
20. This strategy has been utilized for the synthesis of azepines and benzazepines: (a) Farina, V.; Eriksson, M. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., de Meijere, A., Eds.: Wiley-Interscience: New York, 2002; Vol. 2, p 2351. (b) Crisp. G. T.; Meyer, A. G. Tetrahedron 1995, 51, 5585. (c) Mori, M.; Chiba, K.; Ban, Y. J. Org. Chem. 1978, 43, 1684.
21. This strategy has been utilized for the synthesis of azepines and benzazepines: (a) Farina, V.; Eriksson, M. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., de Meijere, A., Eds.: Wiley-Interscience: New York, 2002; Vol. 2, p 2351. (b) Crisp. G. T.; Meyer, A. G. Tetrahedron 1995, 51, 5585. (c) Mori, M.; Chiba, K.; Ban, Y. J. Org. Chem. 1978, 43, 1684.
22. This strategy has been utilized for the synthesis of azepines and benzazepines: (a) Farina, V.; Eriksson, M. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., de Meijere, A., Eds.: Wiley-Interscience: New York, 2002; Vol. 2, p 2351. (b) Crisp. G. T.; Meyer, A. G. Tetrahedron 1995, 51, 5585. (c) Mori, M.; Chiba, K.; Ban, Y. J. Org. Chem. 1978, 43, 1684.
23. Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083.
24. Frantz, D. E.; Fassler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000. 122, 1806.
25. Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687.
26. Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91.
27. Kende, A. S.; Mendoza, J. S. Tetrahedron Lett. 1991, 32, 1699.
28. Cowart, M.; Bennett, M. J.; Kerwin, J. F. J. Org. Chem. 1999, 64, 2240.
29. For examples of Pd-catalyzed carbonylations of hydroxylamines, see: (a) Szarka, Z.; Skoda-Foldes, R.; Kollar, L.; Berente, Z.; Horvath, J.; Tuba, Z. Tetrahedron 2000, 56, 5253. (b) Grigg, R.; Major, J. P.; Martin, F. M.; Whittaker, M. Tetrahedron Lett. 1999, 40, 7709. (c) Herbert, J. M.; McNeill, A. H. Tetrahedron Lett. 1998, 39, 2421.
30. For examples of Pd-catalyzed carbonylations of hydroxylamines, see: (a) Szarka, Z.; Skoda-Foldes, R.; Kollar, L.; Berente, Z.; Horvath, J.; Tuba, Z. Tetrahedron 2000, 56, 5253. (b) Grigg, R.; Major, J. P.; Martin, F. M.; Whittaker, M. Tetrahedron Lett. 1999, 40, 7709. (c) Herbert, J. M.; McNeill, A. H. Tetrahedron Lett. 1998, 39, 2421.
31. For examples of Pd-catalyzed carbonylations of hydroxylamines, see: (a) Szarka, Z.; Skoda-Foldes, R.; Kollar, L.; Berente, Z.; Horvath, J.; Tuba, Z. Tetrahedron 2000, 56, 5253. (b) Grigg, R.; Major, J. P.; Martin, F. M.; Whittaker, M. Tetrahedron Lett. 1999, 40, 7709. (c) Herbert, J. M.; McNeill, A. H. Tetrahedron Lett. 1998, 39, 2421.
32. Brown, H. C.; Choi, Y. M. J. Org. Chem. 1982, 47, 3153.