Synthesis of (+)-CP-263,114 [20]

Journal of the American Chemical Society

Volumn 122, Issue 30, 2000, Pages 7424-7425

  Chen, Chuo ^a   Layton, Mark E ^a   Sheehan, Scott M ^a   Shair, Matthew D ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CP 263 114; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID;

ALKYLATION; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; LETTER; SYNTHESIS;

EID: 0034596347     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001958x     Document Type: Letter

References (36)

1. (a) Dabrah, T. T.; Harwood: H. L.; Huang, L. G.; Jankovich, N. D.; Kaneko, T.; Li, J.-C.; Lindsey, S.; Moshier, P. M.; Subashi, T. A.; Therrien, M.; Watts, P. C. J. Antibiot. 1997, 50, 1-7.
2. (b) Dabrah, T. T.; Kaneko, T.; Massefski, W., Jr.; Whipple, E. B. J. Am. Chem. Soc. 1997, 119, 1594-1598.
3. (a) Nicolaou, K. C.; Harter, M. W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196.
4. (b) Nicolaou, K. C.; Postema, M. H. D.; Miller, N. D.; Yang, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823.
5. (c) Davies, H. M. L.; Calvo, R.; Ahmed, G. Tetrahedron Lett. 1997, 38, 1737-1740.
6. (d) Sgarbi, P. W. M.; Clive, D. L. Chem. Commun. 1997, 2158-2160.
7. (e) Armstrong, A.; Critchley, T. J.; Mortlock, A. A. Synlett 1998, 552-553.
8. (f) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 1877-1880.
9. (g) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 1880-1882.
10. (h) Waizumi, N.; Itoh, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 6015-6018.
11. (i) Bio, M. M.; Leighton, J. L. J. Am. Chem. Soc. 1999, 121, 890-891.
12. (j) Nicolaou, K. C.; Baran, P. S.; Jautelat, R.; He, Y.; Fong, K. C.; Choi, H.-S.; Yoon, W. H.; Zhong, Y.-L. Angew. Chem., Int. Ed. 1999, 38, 549-552.
13. (k) Clive, D. L. J.; Sun, S.; He, X.; Zhang, J.; Gagliardini, V. Tetrahedron Lett. 1999, 40, 4605-4609.
14. (l) Yoshimitsu, T.; Yanagiya, M.; Nagaoka, H. Tetrahedron Lett. 1999, 40, 5215-5218.
15. (m) Sulikowski, G. A.; Agnelli, F.; Corbett, M. A. J. Org. Chem. 2000, 65, 337-342. For recent reviews, see:
16. (n) Hepworth, D. Chem. Ind. (London) 2000, 2, 59.
17. (o) Starr, J. T.; Carreira, E. M. Angew. Chem., Int. Ed. 2000, 39, 1415-1421.
18. Meng, D.; Qiang, T.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1999, 38, 3197-3201.
19. (a) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Choi, H. S.; Yoon, W. H.; He, Y.; Fong, K. C. Angew. Chem., Int. Ed. 1999, 38, 1669-1675.
20. (b) Nicolaou, K. C.; Baran, P. S.; Zhong, Y. L.; Fong, K. C.; He, Y.; Yoon, W. H.; Choi, H. S. Angew. Chem., Int. Ed. 1999, 38, 1676-1678.
21. (c) Nicolaou, K. C.; Jung, J.-K.; Yoon, W. H.; He, Y.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 1829-1832.
22. Chen, C.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 1998, 120, 10784-10785.
23. The synthesis of vinyl stannane 4 is described in the Supporting Information.
24. Mander, L. N.; Sethi, S. P. Tetrahedron Lett. 1983, 24, 5425.
25. For a comprehensive review of the CBS catalyst, see: Corey, E. J. and Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
26. For examples of kinetic resolution using the oxazaborolidine-catalyzed reduction, see: (a) Kurosu, M.; Kishi, Y. J. Org. Chem. 1998, 63, 6100-6101. (b) Schmalz, H.; Jope, H. Tetrahedron 1998, 54, 3457-3464. (c) Bringmann, G.; Hinrichs, J.; Kraus, J.; Wuzik, A.; Schulz, T. J. Org. Chem. 2000, 65, 2517-2527.
27. For examples of kinetic resolution using the oxazaborolidine-catalyzed reduction, see: (a) Kurosu, M.; Kishi, Y. J. Org. Chem. 1998, 63, 6100- 6101. (b) Schmalz, H.; Jope, H. Tetrahedron 1998, 54, 3457-3464. (c) Bringmann, G.; Hinrichs, J.; Kraus, J.; Wuzik, A.; Schulz, T. J. Org. Chem. 2000, 65, 2517-2527.
28. For examples of kinetic resolution using the oxazaborolidine-catalyzed reduction, see: (a) Kurosu, M.; Kishi, Y. J. Org. Chem. 1998, 63, 6100- 6101. (b) Schmalz, H.; Jope, H. Tetrahedron 1998, 54, 3457-3464. (c) Bringmann, G.; Hinrichs, J.; Kraus, J.; Wuzik, A.; Schulz, T. J. Org. Chem. 2000, 65, 2517-2527.
29. Compound 7 was synthesized in eight steps from R-glyceraldehyde acetonide. For details see the Supporting Information.
30. Evans, D. A.; Golob, A. M. J. Am. Chem. Soc. 1975, 97, 4765-4766.
31. 3CH; most likely it is modulating the acidity of the reaction.
32. The modest yield of the Arndt - Eistert homologation is more indicative of the extreme sensitivity of derivatives of 14 rather than the inefficiency of the reactions.
33. 3 in a Pd-catalyzed carbonylation, see: Kayaki, Y.; Noguchi, Y.; Iwasa, S.; Ikariya, T.; Noyori, R. Chem. Commun. 1999, 1235-1236.
34. 1H NMR analysis unequivocally proved its identitiy, it always contained a small amount of u proton-hearing compound unassociated with (+)-1.
35. Sheehan, S. M.; Lalic, G.; Chen, J. Shair, M. D. Angew. Chem., Int. Ed. 2000. In Press.
36. Griffiths, C.; Leadbeater, N. E. Tetrahedron Lett. 2000, 41, 2487-2490.