Total synthesis of (-)-lentiginosine

Tetrahedron Asymmetry

Volumn 19, Issue 6, 2008, Pages 746-750

  Chandrasekhar, S ^a   Vijaykumar, B V D ^a   Pratap, T V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCERALDEHYDE; LENTIGINOSINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DIASTEREOISOMER; EPOXIDATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 41449088123     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.02.017     Document Type: Article

References (22)

1. Walker B.D., Kowalski M., Goh W.C., Kowarsky K., Krieger M., Rosen W.C., Rohrschneider L.R., Haseltine W.A., and Sodroski J. Proc. Natl. Acad. Sci. U.S.A. 84 (1987) 8120-8124
2. Karpas A., Fleet G.W.J., Dwek R.A., Petursson S., Namgoong S.K., Ramsden N.G., Jacob G.S., and Rademacher T.W. Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 9229-9233
3. Winkler D.A., and Holan G. J. Med. Chem. 32 (1989) 2084-2089 and references cited therein
4. Review:. Burgess K., and Henderson I. Tetrahedron 48 (1992) 4045-4066
5. Junge B., Matzke M., and Stoltefuss J. In: Kuhlmann J., and Puls W. (Eds). Handbook of Experimental Pharmacology Vol. 119 (1996), Springer, Berlin, Heidelberg, New York 411-482
6. Elbein, A. D.; Molyneux, R. J. In Comprehensive Natural Products Chemistry; Pinto, B. M., Ed.; Barton, D. H. R., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: UK, 1999; Vol. 3, Chapter 7.
7. Asano N., Nash R.J., Molyneux R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 11 (2000) 1645-1680
8. Pastuszak I., Molyneux R.J., James L.F., and Elbein A.D. Biochemistry 29 (1990) 1886-1891
9. Nukui S., Sodeoka M., Sasai H., and Shibasaki M. J. Org. Chem. 60 (1995) 398-404
10. McCaig A.E., Meldrum K.P., and Wightman R.H. Tetrahedron 54 (1998) 9429-9446
11. Raghavan S., and Sreekanth T. Tetrahedron: Asymmetry 15 (2004) 565-570
12. Michael J.P. Nat. Prod. Rep. 22 (2005) 603-626
13. Angle S.R., Bensa D., and Belanger D.S. J. Org. Chem. 72 (2007) 5592-5597 (Ref. 2-4 therein)
14. Cardona F., Goti A., and Brandi A. Eur. J. Org. Chem. (2007) 1551-1565
15. Brandi A., Cicchi S., Cordero M., Frignoli R., Goti A., Picasso S., and Vogel P. J. Org. Chem. 60 (1995) 6806-6812
16. Sugiyama T., Sugawara H., Watanabe M., and Yamashita K. Agric. Biol. Chem. 48 (1984) 1841-1844
17. Yoshida J., Nakagawa M., Seki H., and Hino T. J. Chem. Soc., Perkin Trans. 3 1 (1992) 343-350
18. Fuwa H., Okamura Y., and Natsugari H. Tetrahedron 60 (2004) 5341-5352
19. Buck M., and Michael Chong J. Tetrahedron Lett. 42 (2001) 5825-5827
20. Takano S., Iwabuchi Y., and Ogasawara K. Synlett (1991) 548-550
21. This cyclization is according to Baldwin's rules for ring closures, a formally disfavoured process. However, Hevko et al. have reported a similar epoxide-opening reaction under basic conditions, where the product of the 5-endo-cyclization is preferred over that from a 4-exo process. Baldwin J.E. J. Chem. Soc., Chem. Commun. (1976) 734-736 (Ref. 1,3 there in)
22. Hevko J.M., Dua S., Talyor M.S., and Bowie J.H. J. Chem. Soc., Perkin Trans. 2 (1998) 1629-1634