Strain-release rearrangement of N-vinyl-2-arylaziridines. Total synthesis of the anti-leukemia alkaloid (-)-deoxyharringtonine

Journal of the American Chemical Society

Volumn 128, Issue 32, 2006, Pages 10370-10371

  Eckelbarger, Joseph D ^a   Wilmot, Jeremy T ^a   Gin, David Y ^a,b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTILEUKEMIC AGENT; AZIRIDINE DERIVATIVE; CEPHALOTAXINE; DEOXYHARRINGTONINE; VINYL DERIVATIVE;

ACYLATION; ADDITION REACTION; ARTICLE; CYCLOADDITION; DIASTEREOISOMER; DRUG SYNTHESIS; ELIMINATION REACTION; ISOMERIZATION; OXIDATION; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRAIN RELEASE REARRANGEMENT;

ANIMALS; ANTINEOPLASTIC AGENTS; AZIRIDINES; HARRINGTONINES; MOLECULAR STRUCTURE;

EID: 33747599646     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja063304f     Document Type: Article

References (36)

1. (a) Miah, M. A. J.; Hudlicky, T.; Reed, J. W. The Alkaloids: Academic Press: New York, 1998; Vol. 51, pp 199-269.
2. (b) Morita, H.; Arisaka, M.; Yoshida, N.; Kobayashi, J. Tetrahedron 2000, 56, 2929-2934.
3. (a) Weinreb, S. M.; Auerbach, J. J. Am. Chem. Soc. 1975, 97, 2503-2506.
4. (b) Semmelhack, M. F.; Chong, B. P.; Stauffer, R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97, 2507-2516.
5. (c) Shingo, Y.; Yamamoto, Y.; Yoshida, S.; Hanaoka, M. Chem. Pharm. Bull. 1988, 36, 4229-4231.
6. (d) Kuehne, M. E.; Bornmann, W. G.; Parsons, W. H.; Spitzer, T. D.; Blount, J. F.; Zubieta, J. J. Org. Chem. 1988, 53, 3439-3450.
7. (e) Burkholder, T. P.; Fuchs, P. L. J. Am. Chem. Soc. 1990, 112, 9601-9613.
8. (f) Ikeda, M.; Okano, M.; Kosaka, K.; Kido, M.; Ishibashi, H. Chem. Pharm. Bull. 1993, 41, 276-281.
9. (g) Lin, X.; Kavash, R. W.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 9791-9792.
10. (h) Isono, N.; Mori, M. J. Org. Chem. 1995, 60, 115-119.
11. (i) Tietze, L. F.; Schirok, H. J. Am. Chem. Soc. 1999, 121, 10264-10269.
12. (j) Ikeda, M.; El Bialy, S. A. A.; Hirose, K.; Kotake, M.; Sato, T.; Bayomi, S. M. M.; Shehata, I. A.; Abdelal, A. M.; Gad, L. M.; Yakura, T. Chem. Pharm. Bull. 1999, 47, 983-987.
13. (k) Koseki, Y.; Sato, H.; Watanabe, Y.; Nagasaka, T. Org. Lett. 2002, 4, 885-888.
14. (l) Li, W. Z.; Wang, Y. Org. Lett. 2003, 5, 2931-2934.
15. (m) Planas, L.; Perard-Viret, J.; Royer, J. J. Org. Chem. 2004, 69, 3087-3092.
16. (a) Mikolajczak, K. L.; Powell, R. G.; Smith, C. R., Jr. Tetrahedron 1972, 28, 1995-2001.
17. (b) For a semi-synthesis of 1, see: Mikolajczak, K. L.; Smith, C. R., Jr.; Weisleder, D.; Kelly, T. R.; McKenna, J. C.; Christenson, P. A. Tetrahedron Lett. 1974, 15, 283-286.
18. (c) Kelly, T. R.; McNutt, R. W., Jr.; Montury, M.; Tosches, N. P.; Mikolajczak, K. L.; Smith, C. R., Jr.; Weisleder, D. J. Org. Chem. 1979, 44, 63-67.
19. Deoxyharringtonine (1) is isolated in <0.01% yield of the plant dry weight.
20. (a) Scheiner, P. J. Org. Chem. 1967, 32, 2628-2630.
21. (b) Figeys, H. P.; Jammar, R. Tetrahedron Lett. 1980, 21, 2995-2998.
22. Tanida, H.; Okada, T.; Kotera, K. Bull. Chem. Soc. Jpn. 1973, 46, 934-938.
23. A stepwise pathway, involving formation of a cationic p-quinone methide and subsequent 7-exo cyclization, cannot be discounted.
24. Ali, S. M.; Ramesh, K.; Borchardt, R. T. Tetrahedron Lett. 1990, 31, 1509-1512.
25. Convergence of both diastereomers of 11 to form 12 may arise from either direct [3,3]-rearrangement of both diastereomers, benzylic epimerization of 11 prior to [3,3]-rearrangement, or a stepwise mechanism (see ref 7).
26. Epperson, M. T.; Gin, D. Y. Angew. Chem., Int. Ed. 2002, 41, 1778-1780.
27. Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am. Chem. Soc. 1995, 117, 5166-5167.
28. β-Approach of the dipolarophile in the cycloaddition followed by C5 epimerization via transannular rupture and reclosure (ref 2g) to form 15 cannot be discounted.
29. Kunzer, H.; Stahnke, M.; Sauer, G.; Wiechert, R. Tetrahedron Lett. 1991, 32, 1949-1952.
30. Clarke, P. A.; Holton, R. A.; Kayaleh, N. E. Tetrahedron Lett. 2000, 41, 2687-2690.
31. (a) Robin, J.-P.; Dhal, R.; Dujardin, G.; Girodier, L.; Mevellec, L.; Poutot, S. Tetrahedron Lett. 1999, 40, 2931-2934 and references therein.
32. (b) Keller, L.; Dumas, F.; d'Angelo, J. Tetrahedron Lett. 2001, 42, 1911-1913.
33. For an acylation of 2 in the semi-synthesis of harringtonine, see ref 3c.
34. Hoye, T. R.; Peterson, B. H.; Miller, J. D. J. Org. Chem. 1987, 52, 1351-1353.
35. Seebach, D.; Naef, R.; Calderari, G. Tetrahedron 1984, 40, 1313-1324.
36. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.