De novo asymmetric approach to 8a-epi-Swainsonine

Heterocycles

Volumn 79, Issue C, 2009, Pages 521-529

  Coral, Jason A ^a   Guo, Haibing ^a   Shan, Mingde ^a   O'Doherty, George A ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

8a epi Swainsonine; Acylfuran; De Novo Asymmetric Synthesis; Noyori Reduction; Swainsonine

Indexed keywords

EID: 67149147439     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(D)12     Document Type: Article

References (26)

1. Guo H., and O'Doherty G.A. Org. Lett 8 (2006) 1609
2. Guo H., and O'Doherty G.A. Tetrahedron 64 (2008) 304
3. Abrams J.N., Babu R.S., Guo H., Le D., Le J., Osbourn J.M., and O'Doherty G.A. J. Org. Chem. 73 (2008) 1935
4. Dudot B., Micouin L., Baussanne I., and Royer J. Synthesis (1999) 688
5. Keck G.E., and Romer E.R. J. Org. Chem. 58 (1993) 6083
6. Bi J., and Aggarwal V.K. Chem. Commun. (2008) 120
7. Kim Y.G., and Cha J.K. Tetrahedron Lett. 30 (1989) 5721
8. Tadano K., Hotta Y., Morita M., Suami T., Winchester B., and Cenci di Bello I. Bull. Chem. Soc. Jpn. 60 (1987) 3667
9. Tadano K., Hotta Y., Morita M., Suami T., Winchester B., and Cenci di Bello I. I. Chem. Lett. (1986) 2105
10. Giovannini A., Savoia D., and Umani-Ronchi A. J. Org. Chem. 54 (1989) 228
11. Fujii A., Hashiguchi S., Uematsu N., Ikariya T., and Noyori R. J. Am. Chem. Soc. 118 (1996) 2521
12. Noyori R., and Ohkuma T. Angew. Chem. Int. Ed. 40 (2001) 40
13. Guo H., and O'Doherty G.A. Org. Lett. 7 (2005) 3921
14. Haukaas M.H., and O'Doherty G.A. Org. Lett. 3 (2001) 3899 And see ref. 2
15. Achmatowicz O., and Bielski R. Carbohydr. Res. 55 (1977) 165
16. Babu R.S., and O'Doherty G.A. J. Am. Chem. Soc. 125 (2003) 12406
17. Babu R.S., Zhou M., and O'Doherty G.A. J. Am. Chem. Soc. 126 (2004) 3428 For examples see
18. Guppi S.R., Zhou M., and O'Doherty G.A. Org. Lett. 8 (2006) 293
19. Zhou M., and O'Doherty G.A. Org. Lett. 8 (2006) 4339
20. Shan M., and O'Doherty G.A. Org. Lett 8 (2006) 5149
21. Guo H., and O'Doherty G.A. Angew. Chem. Int. Ed. 46 (2007) 5206
22. Guo H., and O'Doherty G.A. J. Org. Chem. 73 (2008) 5211
23. Shing T.K.M., Tarn E.K.W., Tai V.W.-F., Chung I.H.F., and Jiang Q. Chem. Eur. J. 2 (1996) 50
24. Only new procedures are reported in this paper, for the conversion of 7 to 6 and 5 to 3, see ref. 2c.
25. The ratios of desired product 7 over ester 12 could range from 1.5 to 2.0 in different runs.
26. K. Saigo, M. Usui, K. Kikuchi, E. Shimada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1977, 50, 1863.