Chemoenzymatic approaches to lycorine-type amaryllidaceae alkaloids: Total syntheses of enf-lycoricidine, 3-epi-ent-lycoricidine, and 4-deoxy-3-epi-ent- lycoricidine

Organic Letters

Volumn 9, Issue 18, 2007, Pages 3683-3685

  Matveenko, Maria ^a   Kokas, Okanya J ^a   Banwell, Martin G ^a   Willis, Anthony C ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

4 DEOXY 3 EPI ENT LYCORICIDINE; 4-DEOXY-3-EPI-ENT-LYCORICIDINE; AMARYLLIDACEAE ALKALOID; ENZYME; LYCORICIDINE; PHENANTHRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMARYLLIDACEAE ALKALOIDS; CATALYSIS; ENZYMES; MOLECULAR STRUCTURE; PHENANTHRIDINES; STEREOISOMERISM;

EID: 34548529509     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701552r     Document Type: Article

References (34)

1. For reviews dealing with this class of alkaloid, see: (a) Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1987; Vol. 30, p 251.
2. (b) Hoshino, O. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 51, p 323.
3. (c) Jin, Z. Nat. Prod. Rep. 2003, 20, 606.
4. For useful points on entry into the literature concerned with the biological properties of lycorine-type alkaloids and their analogues, see: (a) Pettit, G. R.; Melody, N. J. Nat. Prod. 2005, 68, 207.
5. (b) McNulty, J.; Larichev, V.; Pandey, S. Bioorg. Med. Chem. Lett. 2005, 15, 5315.
6. (c) Pettit, G. R.; Eastham, S. A.; Melody, N.; Orr, B.; Herald, D. L.; McGregor, J.; Knight, J. C.; Doubek, D. L.; Pettit, G. R., III; Garner, L. C.; Bell, J. A. J. Nat. Prod. 2006, 69, 7.
7. (a) Hudlicky, T. J. Heterocycl. Chem. 2000, 37, 535.
8. (b) Rinner, U.; Hudlicky, T. Synlett 2005, 365.
9. (c) Chapleur, Y.; Chrétien, F.; Ibn Ahmed, S.; Khaldi, M. Curr. Org. Synth. 2006, 3, 341.
10. 3 see: (a) Zhang, H.; Padwa, A. Synlett 2006, 2317.
11. (b) Zhang, H.; Padwa, A. Org. Lett. 2006, 8, 247.
12. (c) Shukla, K. H.; Boehmler, D. J.; Bogacyzk, S.; Duvall, B. R.; Peterson, W. A.; McElroy, W. T.; DeShong, P. Org. Lett. 2006, 8, 4183.
13. (d) Li, M.; Wu, A.; Zhou, P. Tetrahedron Lett. 2006, 47, 3707.
14. (e) Crich, D.; Krishnamurthy, V. Tetrahedron 2006, 62, 6830.
15. (f) Shin, I.-J.; Choi, E.-S.; Cho, C.-G. Angew. Chem., Int. Ed. 2007, 46, 2303.
16. (g) Padwa, A.; Zhang, H. J. Org. Chem. 2007, 72, 2570.
17. For reviews on methods for generating cis- 1,2-dihydrocatechols by microbial dihydroxylation of the corresponding aromatics, as well as the synthetic applications of these metabolites, see: (a) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichim. Acta 1999, 32, 35.
18. (b) Banwell, M. G.; Edwards, A. J.; Harfoot, G. J.; Jolliffe, K. A.; McLeod, M. D.; McRae, K. J.; Stewart, S. G.; Vögtle, M. Pure Appl. Chem. 2003, 75, 223.
19. (c) Johnson, R. A. Org. React. 2004, 63, 117.
20. Banwell, M. G.; McRae, K. J.; Willis, A. C. J. Chem. Soc., Perkin Trans. 1 2001, 2194.
21. Banwell, M. G.; Kokas, O. J.; Willis, A. C. Org. Lett. 2007, 9, 3503.
22. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 1973.
23. Crossland, R. K.; Servis, K. L. J. Org. Chem. 1970, 35, 3195.
24. Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353.
25. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
26. Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockless, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551.
27. Hanessian, S.; Delorme, D.; Dufresne, Y. Tetrahedron Lett. 1984, 25, 2515.
28. Mentzel, U. V.; Tanner, D.; Tonder, J. E. J. Org. Chem. 2006, 71, 5807.
29. Nishikawa, T.; Asai, M.; Ohyabu, N.; Isobe, M. J. Org. Chem. 1998, 63, 188.
30. (a) Overman, L. E. Acc. Chem. Res. 1980, 13, 218.
31. (b) Overman, L. E.; Carpenter, N. E. Org. React. 2005, 66, 1 and references cited therein.
32. Oishi, T.; Ando, K.; Inomiya, K.; Sato, H.; Iida, M.; Chida, N. Org. Lett. 2002, 4, 151.
33. Keck, G. E.; Wager, T. T.; Duarte Rodriquez, J. F. J. Am. Chem. Soc. 1999, 121, 5176.
34. Details of this analysis are provided in the Supporting Information.