A totally stereocontrolled route to N-methyl-γ-amino-β-hydroxy acids: Asymmetric synthesis of the amino acid component of hapalosin

Tetrahedron Letters

Volumn 40, Issue 52, 1999, Pages 9309-9312

  Catasús, Mònica ^a   Moyano, Albert ^a   Pericàs, Miquel A ^a   Riera, Antoni ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Amino alcohols; Antitumour compounds; Asymmetric synthesis; Depsipeptides; Epoxides

Indexed keywords

AMINOALCOHOL; ANTINEOPLASTIC AGENT; DEPSIPEPTIDE; EPOXIDE; HAPALOSIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; METHYLATION; PARTIAL DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033601414     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01953-X     Document Type: Article

References (35)

1. Stratmann, K.; Burgoyne, D. L.; Moore, R. E.; Patterson, G. M. L.; Smith, C. D. J. Org. Chem. 1994, 59, 7219.
2. Pettit, G. R.; Singh, S. B.; Herald, D. L.; Lloyd-Williams, P.; Kantoci, D.; Burkett, D. D.; Barcokzy, J.; Hogan, F.; Wardlaw, T. R. J. Org. Chem. 1994, 59, 6287, and refs. cited therein.
3. (a) Maugras, I.; Poncet, J.; Jouin, P. Tetrahedron 1990, 46, 2807.
4. (b) Shiori, T.; Hayashi, K.; Hamada, Y. Tetrahedron 1993, 49, 1913.
5. (c) Okuno, T.; Ohmori, S.; Nishiyama, S.; Yamamura, S.; Nakamura, K.; Houk, K. N.; Okamoto, K. Tetrahedron 1996, 52, 14723.
6. (a) Kano, S.; Yokomatsu, T.; Shibuya, S. J. Org. Chem. 1989, 54, 513.
7. (b) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocycles 1990, 31, 1597.
8. (c) Roux, F.; Maugras, V.; Poncet, J.; Niel, G.; Jouin, P. Tetrahedron 1994, 50, 5345.
9. (d) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Chem. Commun. 1999, 317.
10. Synthetic studies on Hapalosin: (a) Ghosh, A. K.; Liu, W.; Xu, Y.; Chen, Z. Angew. Chem. Int. Ed. Engl. 1996, 35, 74.
11. (b) Dinh, T. Q.; Armstrong, R. W. J. Org. Chem. 1995, 60, 8118.
12. (c) Dinh, T. Q.; Du, X.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6606.
13. (d) Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 3467.
14. (e) Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557.
15. (f) Wagner, B.; Islas González, G.; Tran Hun Dau, M. E.; Zhu, J. Bioorg. Med. Chem. 1999, 7, 737.
16. (g) Haddad, M.; Botuha, C.; Larchevêque, M. Synlett 1999, 1118, and refs. cited therein.
17. The term "multidrug-resistance" refers to the ability of a tumor cell to develop cross resistance to several structurally unrelated anticancer agents. See: (a) Chabner, B. A.; Collins, J. M. Cancer Chemotherapy: Principles and Practice; J. B. Lippincott Co., Philadelphia: 1990.
18. (b) Simon, S. M.; Schindler, M. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3497.
19. (c) Gottesman, M. M.; Pastan, I. Annu. Rev. Biochem. 1993, 62, 385.
20. (d) Endicott, J. A.; Ling, V. Annu. Rev. Biochem. 1989, 58, 137.
21. (e) Kartner, N.; Riordan, J. R.; Ling, V. Science 1983, 221, 1285.
22. Castejón, P.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1996, 52, 7063.
23. Bennet, F.; Girijavallabhan, V. M.; Patel, N. J. Chem. Soc., Chem. Commun. 1993, 737.
24. (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
25. (b) Johnson, R. A.; Sharpless, K. B. in Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers, New York: 1993, p. 101.
26. (c) Katsuki, T.; Martín, V. S. Org. React. 1996, 48, 1.
27. Caron, M.; Carlier, P. R.; Sharpless, K. B. J. Org. Chem. 1988, 53, 5185.
28. Bodanszky, M.; Bodanszky, A. The Practice of Peptide Synthesis; Springer-Verlag, Berlin Heidelberg: 1984, p. 12.
29. Saito, S.; Nakajima, H.; Inaba, M.; Moriwake, T. Tetrahedron Lett. 1989, 30, 837.
30. Castejón, P.; Pastó, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1995, 36, 3019.
31. For other approaches to the synthesis of enantiopure N-protected aminoalkyl epoxides, see: Kurihara, M.; Ishii, K.; Kasahara, Y.; Miyata, N. Tetrahedron Lett. 1999, 40, 3183, and refs. cited therein.
32. For a synthesis of the threo isomer of 7a from (S)-N-methyl phenylalanine, see: Beier, C.; Schaumann, E.; Adiwidjaja, G. Synlett 1998, 41.
33. Abiko, A.; Roberts, J. C.; Takemasa, T.; Masamune, S. Tetrahedron Lett. 1986, 27, 4537.
34. For a total synthesis of Hapalosin proceeding through 11b, see ref. 5g.
35. 3Si: C, 65.99; H, 9.15; N, 6.69. Found: C, 66.00; H, 9.18; N, 6.62 (signals marked with an asterisk correspond to a rotamer).