Highly efficient formal synthesis of cephalotaxine, using the stevens rearrangement-acid lactonization sequence as a key transformation

Journal of Organic Chemistry

Volumn 74, Issue 5, 2009, Pages 2213-2216

  Sun, Mo Ran ^a   Lu, Hong Tao ^a   Wang, Yan Zhi ^a   Yang, Hua ^a   Liu, Hong Min ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL BROMIDES; ANTI-TUMOR ACTIVITIES; CEPHALOTAXINE; FORMAL SYNTHESIS; LACTONIZATION; STRUCTURAL FEATURES;

ACIDS;

CEPHALOTAXINE;

ACID LACTONIZATION SEQUENCE; ARTICLE; DRUG SYNTHESIS; DRUG TRANSFORMATION; LACTONIZATION; STEVENS REARRANGEMENT;

ACIDS; HARRINGTONINES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 64249124471     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8025252     Document Type: Article

References (29)

1. For reviews see: (a) Huang, L.; Xue, Z. In The Alkaloids: Brossi, A., Ed.; Academic Press: New York, 1984; Vol. 23, pp 157-226.
2. (b) Hudlicky, T.; Kwart, L. D.; Reed, J. W. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.: John Wiley and Sons: New York, 1987; Vol. 5, pp 639-690.
3. (c) Jalil Miah, M. A.; Hudlicky, T.; Reed, J. W. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1998; Vol. 51, pp 199-269.
4. For a recent total synthesis, see: Hameed, A.; Blake, A. J.; Hayes, C. J. J. Org. Chem. 2008, 78, 8045, and references cited therein.
5. For possible transformation from 3 to 1 via an alternative pathway, see relevant total synthesis of cephalotaxine: (a) Kuehne, M. E.; Bornmann, W. G.; Parsons, W. R; Spitzer, T. D.; Blount, J. F.; Zubieta, J. J. Org. Chem. 1988, 53, 3439.
6. (b) Planas, L.; Perard-Viret, J.; Royer, J. J. Org. Chem. 2004, 69, 3087.
7. (c) Sha, C. K.; Youns, J. J.; Yeh, C. P.; Chang, S. C.; Wang, S. L. J. Org. Chem. 1991, 56, 2694.
8. (d) Isono, N.; Mori, M. J. Org. Chem. 1995, 60, 115.
9. (e) Tieze, L. F.; Shirok, H. J. Am. Chem. Soc. 1999, 121, 10264.
10. (f) Ikeda, M.; Hirose, K.; El, Bialy, S. A. A.; Sato, T.; Yakura, T.; Bayoma, S. M. M. Chem. Pharm. Bull. 1998, 46, 1084.
11. (g) Suga. S.; Watanabe, M.; Yoshida, J. I. J. Am. Chem. Soc. 2002, 124, 14824.
12. (h) Semmelhack, M. F.; Chong, B. P.; Stauffer, R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97, 2507.
13. Yasuda, S.; Yamada, T.; Hanoka, M. Tetrahedron Lett. 1986, 27, 2023.
14. Li, W.-D. Z.; Wang, X.-W. Org. Lett. 2007, 9, 1211.
15. (a) Molander, G. A.; Hiersemann, M. Tetrahedron Lett. 1997, 25, 4347.
16. (b) Shiina, I.; Oshiumi, H.; Hashizume, M.; Yama, Y.-S.; Ibuka, R. Tetrahdron Lett. 2004, 45, 543.
17. Li, W.-D. Z.; Wang, Y.-Q. Org. Lett. 2003, 5, 2931.
18. 3CN, DMSO, rt → reflux (Figure presented)
19. 2;. Viscous brown jelly was produced during the course of the following reaction (Figure presented)
20. For reported acid-lactonization reaction of γ-en-carboxylate, see: (a) Amonkar, C. P.; Tuve, S. G.; Parameswaran, P. S. Synthesis 2005, 14, 2341.
21. (b) Guo, M.; Varady, L. Tetrahedron Lett. 2002, 43, 3677.
22. (c) IIa Hiriyakkanavar, A.-D.; Junjappa, H. Tetrahedron 1987, 43, 5367.
23. (d) Tiecco, M.; Tingoli, M.; Testaferri, L.; Bartoli, D. Synth. Commun. 1989, 19, 2817.
24. Jung, M. E.; Min, S.-J. Tetrahedron 2007, 63, 3682.
25. Demark, M. E.; Fu, J. Org. Lett. 2002, 4, 1951.
26. tBu/THF system, which furnished the amino spirocvclopentenone 3a. For information on this svstem, see: Freiria, M.; Whitehead, A. J.; Tocher, D. A.; Motherwell. W. B. Tetrahedron 2004, 60, 2673.
27. Wright, S. W.; Ammirati, M. J.; Andrews, K. M.; Brodeur, A. M.; et al. J. Med. Chem. 2006, 49, 3068.
28. Ahn, J.-B.; Yun, C.-S.; Kim, K. H.; Ha, D.-C. J. Org. Chem. 2000, 65, 9249.
29. Pandolfi, E.; Comas, H. Tetrahedron Lett. 2003, 44, 4631.