Construction of Consecutive Chiral Non-Racemic Quaternary and Tertiary Carbon Centers: A Short Synthetic Route to (-)-Acetomycin

European Journal of Organic Chemistry

Volumn , Issue 20, 2003, Pages 3909-3912

  Uenishi, Jun'ichi ^a   Kawatsura, Motoi ^a   Ikeda, Daiji ^a   Muraoka, Nobuhiro ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Diastereoselectivity; Natural products; P ligands; Palladium; Quaternary carbon center

Indexed keywords

2 (DIPHENYLPHOSPHANYL)CARBOXYLIC ACID; ACETOACETIC ACID; ACETOMYCIN; CARBON; CARBOXYLIC ACID DERIVATIVE; LIGAND; PALLADIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0242386456     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300504     Document Type: Article

References (46)

1. [1a] J. Christoffers, A. Mann, Angew. Chem. Int. Ed. 2001, 40, 4591-4597.
2. [1b] E. J. Corey, A. G-. Perez, Angew. Chem. Int. Ed. 1998, 37, 389-401.
3. [1c] K. Fuji, Chem. Rev. 1993, 93, 2037-2066.
4. Alkylation and aldol addition: [2a] Y. Yamashita, K. Odashima, K. Koga, Tetrahedron Lett. 1999, 40, 2803-2806.
5. [2b] Z. Chen, G. Zhu, Q. Jiang, D. Xiao, P. Cao, X. Zhang, J. Org. Chem. 1998, 63, 5631-5635.
6. [2c] M. Murakata, T. Jono, Y. Mizuno, O. Hoshino, J. Am. Chem. Soc. 1997, 119, 11713-11714.
7. [2d] S. E. Denmark, J. Fu, Org. Lett. 2002, 4, 1951-1953.
8. [2e] J. W. J. Kennedy, D. G. Hall, J. Am. Chem. Soc. 2002, 124, 898-899.
9. D. A. Evans, J. S. Johnson, in Comprehensive Asymmetric Catalysis Vol. III (Eds.: E. M. Jacobsen, A. Pfaltz, H. Yamamoto), Springer: Berlin, 1999, pp. 1177-1235.
10. [4a] M. Shibasaki, C. D. J. Boden, T. Takemoto, Tetrahedron 1997, 53, 7371-7395.
11. [4b] L. E. Overman, Pure & Appl. Chem. 1994, 66, 1423-1434.
12. [5a] K. Funabashi, H. Ratni, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 10784-10785 (cyanation).
13. [5b] M. Ori, N. Toda, K. Takami, K. Tago, H. Kogen, Angew. Chem. Int. Ed. 2003, 42, 2540-2543 (rearrangement).
14. [5c] Y. Kita, A. Furukawa, J. Futamura, K. Ueda, Y. Sawama, H. Hamamoto, H. Fujioka, J. Org. Chem. 2001, 66, 8779-8786 (rearrangement).
15. [5d] E. Schoffers, A. Golebiowski, C. R. Johnson, Tetrahedron 1996, 52, 3769-3826 (enzymatic method).
16. [6a] G. Helmchen, A. Pfaltz, Acc. Chem. Res. 2000, 33, 336-345.
17. [6b] B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
18. [6c] A. Pfaltz, M. Lautens, in Comprehensive Asymmetric Catalysis Vol. II (Eds.: E. M. Jacobsen, A. Pfaltz, H. Yamamoto), Springer: Berlin, 1999, pp 833-884.
19. [6d] T. Hayashi, J. Organomet. Chem. 1999, 576, 195-202.
20. [6e] M. Johannsen, K. A. Jorgensen, Chem. Rev. 1998, 1689-1708.
21. [7a] B. M. Trost, X. Ariza, Angew. Chem. Int. Ed. Engl. 1997, 36, 2635-2637.
22. [7b] R. Kuwano, Y. Ito, J. Am. Chem. Soc. 1999, 121, 3236-3237.
23. [7c] B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 1999, 121, 6759-6760.
24. [7d] B. M. Trost, G. M. Schroeder, J. Kristensen, Angew. Chem. Int. Ed. 2002, 41, 3492-3495.
25. [7e] R. Kuwano, K. Uchida, Y. Ito, Org. Lett. 2003, 5, 2177-2179.
26. [8a] B. M. Trost, F. D. Toste, J. Am. Chem. Soc. 1999, 121, 4547-4554.
27. [8b] T. Hayashi, A. Yamamoto, T. Hagihara, J. Org. Chem. 1986, 51, 3236-3237.
28. K. Burgess, L. D. Jennings, J. Am. Chem. Soc. 1991, 113, 6129-6139. Enantiomerically pure 1 was prepared by lipase-catalyzed kinetic acetylation of the corresponding racemic alcohol and the optical purity was determined by HPLC using a chiral column.
29. G. Koch, G. C. Lloyd-Jones, O. Loiseleur, A. Pfaltz, R. Pretot, S. Schaffner, P. Schneider, P. von Matt, Recl. Trav. Chim. Pays-Bas. 1995, 114, 206-210.
30. Ligands L-1 and L-2, were purchased from Aldrich Co. Ltd. Ligands, L-3, L-4, and L-5, were prepared by the procedure in B. M. Trost, R. C. Bunt, R. C. Lemoine, T. L. Calkins, J. Am. Chem. Soc. 2000, 122, 5968-5976.
31. An assignment of the diastereochemistry and absolute stereochemistry was confirmed after converting the predominant (R)-diastereomer to (-)-acetomycin, which is shown in Scheme 4.
32. L. Ettlinger, E. Gäumann, R. Hütter, W. K. Schierlein, F. Kradolfer, L. Neipp, V. Prelog, H. Zähner, Helv. Chim. Acta 1958, 41, 216-219.
33. [14a] K. Tadano, J. Ishihara, S. Ogawa, Tetrahedron Lett. 1990, 31, 2609-2612.
34. [14b] J. Uenishi, T. Okadai, S. Wakabayashi, Tetrahedron Lett. 1991, 32, 3381-3384.
35. [14c] F. E. Ziegler, H. Kim, Tetrahedron Lett. 1993, 34, 7669-7672.
36. [14d] T. J. Sprules, J.-F. Lavallée, J. Org. Chem. 1995, 60, 5041-5047.
37. [14e] S. S. Kinderman, B. L. Feringa, Tetrahedron: Asymmetry 1998, 9, 1215-1222.
38. [15a] K. Tadano, J. Ishihara, S. Ogawa, Tetrahedron Lett. 1990, 31, 2609-2612.
39. [15b] J. Uenishi, T. Okadai, S. Wakabayashi, Tetrahedron Lett. 1991, 32, 3381-3384.
40. [15c] F. E. Ziegler, H. Kim, Tetrahedron Lett. 1993, 34, 7669-7672.
41. [15d] T. J. Sprules, J.-F. Lavallée, J. Org. Chem. 1995, 60, 5041-5047.
42. [15e] S. S. Kinderman, B. L. Feringa, Tetrahedron: Asymmetry 1998, 9, 1215-1222.
43. It is necessary to use methyl ester in this step of the hydrolysis.
44. M. Node, K. Kumar, K. Nishide, S. Ohsugi, T. Miyamoto, Tetrahedron Lett. 2001, 42, 9207-9210.
45. 20 = -157 (c = 0.66, EtOH), was reported in H. Uhr, A. Zeeck, W. Clegg, E. Egert, H. Fuhrer, H. H. Peter, J. Antibiot. 1985, 38, 1684-1690.
46. 21 steps shorter than the first total synthesis of (-)-acetomycin reported by Tadano et al. in ref.[14al