Short synthesis of (+)-cylindricine C by using a catalytic asymmetric Michael reaction with a two-center organocatalyst

Angewandte Chemie - International Edition

Volumn 45, Issue 28, 2006, Pages 4635-4637

  Shibuguchi, Tomoyuki ^a   Mihara, Hisashi ^a   Kuramochi, Akiyoshi ^a   Sakuraba, Shun ^a   Ohshima, Takashi ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Cyclization; Michael addition; Phase transfer catalysis; Spiro compounds; Total synthesis

Indexed keywords

CYCLIZATION; MICHAEL ADDITION; PHASE TRANSFER CATALYSIS; SPIRO COMPOUNDS; TOTAL SYNTHESIS;

CATALYST SELECTIVITY; ORGANIC COMPOUNDS; SALTS;

CATALYST ACTIVITY;

CYLINDRICINE C; FUSED HETEROCYCLIC RINGS; QUINOLONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; SYNTHESIS;

CATALYSIS; HETEROCYCLIC COMPOUNDS, 3-RING; MOLECULAR STRUCTURE; QUINOLONES;

EID: 33746277828     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601722     Document Type: Article

References (37)

1. For representative reviews of tandem reactions in organic synthesis, see: a) J. D. Winkler, Chem. Rev. 1996, 96, 167;
2. b) P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195;
3. c) K. C. Nicolaou, T. Montagnon, S. A. Snyder, Chem. Commun. 2003, 551;
4. d) J. C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001.
5. For general reviews, see: a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
6. b) Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pflatz, H. Yamamoto), Springer, New York, 1999;
7. c) I. Ojima, Catalytic Asymmetric Synthesis, 2nd ed., Wiley, New York, 2000.
8. a) A. J. Blackman, C. Li, D. C. R. Hockless, B. H. Skelton, Tetrahedron 1993, 49, 8645;
9. b) A. J. Blackman, C. Li, Aust. J. Chem. 1994, 47, 1355;
10. c) A. J. Blackman, C. Li, Aust. J. Chem. 1995, 48, 955.
11. a) A. D. Patil, A. J. Freyer, R. Reichwein, B. Carte, L. B. Killmer, L. Faucette, R. K. Johnson, D. J. Faulkner, Tetrahedron Lett. 1997, 38, 363;
12. b) S. Dutta, H. Abe, S. Aoyagi, C. Kibayashi, K. S. Gates, J. Am. Chem. Soc. 2005, 127, 15 004.
13. M. F. Raub, J. H. Cardellina, M. I. Choudhary, C.-Z. Ni, J. Clardy, M. C. Alley, J. Am. Chem. Soc. 1991, 113, 3178.
14. For a review of the synthesis of cylindricines, see: J. Liu, R. P. Hsung, ChemTracts 2005, 18, 321.
15. a) G. A. Molander, M. Ronn, J. Org. Chem. 1999, 64, 5183;
16. b) B. M. Trost, M. T. Rudd, Org. Lett. 2003, 5, 4599;
17. c) S. Canesi, D. Bouchu, M. A. Ciufolini, Angew. Chem. 2004, 116, 4436;
18. Angew. Chem. Int. Ed. 2004, 43, 4336;
19. d) T. Arai, H. Abe, S. Aoyagi, C. Kibayashi, Tetrahedron Lett. 2004, 45, 5921;
20. e) J. Liu, R. P. Hsung, S. D. Peter, Org. Lett. 2004, 6, 3989.
21. a) T. Shibuguchi, Y. Fukuta, Y. Akachi, A. Sekine, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2002, 43, 9539;
22. b) T. Ohshima, T. Shibuguchi, Y. Fukuta, M. Shibasaki, Tetrahedron 2004, 60, 7743;
23. c) A. Okada, T. Shibuguchi, T. Ohshima, H. Masu, K. Yamaguchi, M. Shibasaki, Angew. Chem. 2005, 117, 4640;
24. Angew. Chem. Int. Ed. 2005, 44, 4564.
25. For recent reviews of asymmetric phase-transfer catalysis (PTC) reactions, see: a) K. Maruoka, T. Ooi, Chem. Rev. 2003, 103, 3013;
26. b) M. J. O'Donnell, Acc. Chem. Res. 2004, 37, 506;
27. c) B. Lygo, B. I. Andrews, Acc. Chem. Res. 2004, 37, 518.
28. For the catalytic asymmetric phase-transfer Michael reaction of the glycine Schiff base, see: a) E. J. Corey, M. C. Noe, F. Xu, Tetrahedron Lett. 1998, 39, 5347;
29. b) M. J. O'Donnell, F. Delgado, E. Dominguez, J. de Blas, W. L. Scott, Tetrahedron: Asymmetry 2001, 12, 821;
30. c) S. Arai, R. Tsuji, A. Nishida, Tetrahedron Lett. 2002, 43, 9535;
31. d) T. Akiyama, M. Kara, K. Fuchibe, S. Sakamoto, K. Yamaguchi, Chem. Commun. 2003, 1734;
32. e) B. Lygo, B. Albutt, E. H. M. Kirton, Tetrahedron Lett. 2005, 46, 4461;
33. f) P. V. Ramachandran, S. Madhi, L. Bland-Berry, M. V. R. Reddy, M. J. O'Donnell, J. Am. Chem. Soc. 2005, 127, 13 450.
34. a) K. M. Werner, J. M. de los Santos, S. M. Weinreb, M. Shang, J. Org. Chem. 1999, 64, 8263;
35. b) J. J. Swidorski, J. Wang, R. P. Hsung, Org. Lett. 2006, 8, 777.
36. a) K. Ishizumi, K. Koga, S. Yamada, Chem. Pharm. Bull. 1968, 16, 492;
37. b) G. Kokotos, Synthesis 1990, 299.