Enantioselective synthesis of renieramide

Synlett

Volumn , Issue 15, 2004, Pages 2809-2811

  Lygo, Barry ^a   Humphreys, Luke D ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Amino acids; Asymmetric alkylation; Phase transfer catalysis; Quaternary ammonium salts

Indexed keywords

CYCLOPEPTIDE; ISODITYROSINE; NATURAL PRODUCT; RENIERAMIDE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 10844264057     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-835623     Document Type: Article

References (38)

1. Fry, S. C. Biochem. J. 1982, 204, 449.
2. Zhu, Z. Synlett 1997, 133.
3. K13: (a) Kase, H.; Kaneko, M.; Yamada, K. J. Antibiot. 1987, 40, 450.
4. (b) Yasuzawa, T.; Shirahata, K.; Sano, H. J. Antibiot. 1987, 40, 455.
5. OF-4949-I-IV: (a) Sano, S.; Ikai, K.; Kuroda, H.; Nakamura, T.; Obayashi, A.; Ezure, Y.; Enomoto, H. J. Antibiot. 1986, 39, 1674.
6. (b) Sano, S.; Ikai, K.; Katayama, K.; Takesako, K.; Nakamura, T.; Obayashi, A.; Ezure, Y.; Enomoto, H. J. Antibiot. 1986, 39, 1685.
7. Eurypamides A-D: Reddy, M. V. R.; Harper, M. K.; Faulkner, D. J. Tetrahedron 1998, 54, 10649.
8. Renieramide: (a) Ciasullo, L.; Casapullo, A.; Cutignano, A.; Bifulco, G.; Debitus, C.; Hooper, J.; Gomez-Paloma, L.; Riccio, R. J. Nat. Prod. 2002, 65, 407.
9. (b) Itokawa, H.; Watanabe, K.; Kawaoto, S.; Inoue, T. Jpn. Kokai Tokkyo Koho JP 63203671, 1988.
10. For leading references to the syntheses of K13, OF4949-I-IV and the eurypamides see: (a) Ito, M.; Yamanaka, M.; Kutsumura, N.; Nishiyama, S. Tetrahedron 2004, 60, 5623.
11. (b) Jackson, R. F. W.; Perez-Gonzalez, M. Chem. Commun. 2000, 2423.
12. (c) Bigot, A.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 2000, 41, 4573.
13. (d) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488.
14. (e) Pearson, A. J.; Zhang, P. L.; Lee, K. J. Org. Chem. 1996, 61, 6581.
15. (f) Rao, A. V. R.; Gurjar, M. K.; Reddy, A. B.; Khare, V. B. Tetrahedron Lett. 1993, 34, 1657.
16. (g) Boger, D. L.; Yohannes, D. J. Org. Chem. 1990, 55, 6000.
17. (h) Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111, 1063.
18. (i) Nishiyama, S.; Suzuki, Y.; Yamamura, S. Tetrahedron Lett. 1989, 30, 379.
19. (j) Schmidt, U.; Weller, D.; Holder, A.; Lieberknecht, A. Tetrahedron Lett. 1988, 29, 3227.
20. Lygo, B. Tetrahedron Lett. 1999, 40, 1389.
21. (a) Lygo, B.; Allbutt, B. Synlett 2004, 326.
22. (b) Lygo, B.; Allbutt, B.; James, S. R. Tetrahedron Lett. 2003, 44, 5629.
23. 4NBr as the PTC. Use of catalyst 8 led to similar regioselectivity and yield, but gave 10 with only 50% ee.
24. Reinholtz, E.; Becker, A.; Hagenbruch, B.; Schäfer, S.; Schmitt, A. Synthesis 1990, 1069.
25. (a) Lygo, B.; Andrews, B. I.; Slack, D. Tetrahedron Lett. 2003, 44, 9039.
26. (b) Lygo, B.; Andrews, B. I. Tetrahedron Lett. 2003, 44, 4499.
27. (c) Lygo, B.; Humphreys, L. D. Tetrahedron Lett. 2002, 43, 6677.
28. (d) Lygo, B.; Andrews, B. I.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 2002, 43, 8015.
29. (e) Lygo, B.; Crosby, J.; Lowdon, T. R.; Wainwright, P. G. Tetrahedron 2001, 57, 2391.
30. (f) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403.
31. (g) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron 2001, 57, 6447.
32. (h) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595.
33. For application of a related alkylation to the synthesis of the dityrosine fragment of RP66453 see: Boisnard, S.; Carbonnelle, A.-C.; Zhu, J. Org. Lett. 2001, 3, 2061.
34. +: 697.3489. Found: 697.3528.
35. For an alternative approach to orthogonally protected (S,S)-isodityrosines see: Jorgensen, K. B.; Gautun, O. R. Tetrahedron 1999, 55, 10527.
36. Kiso, Y.; Nakamura, S.; Ito, K.; Ukawa, K.; Kitagawa, K. J. Chem. Soc., Chem. Commun. 1979, 971.
37. 3).
38. 2 carbon of the L-DOPA fragment occurs at δ = 37.7 ppm (not 43.6). We thank Prof. R. Riccio and Dr. A. Casapullo for kindly providing this information.