A new asymmetric synthesis of the natural enantiomer of the indolizidino[8,7-b]indole alkaloid (+)-harmicine

Tetrahedron Letters

Volumn 48, Issue 32, 2007, Pages 5669-5671

  Allin, Steven M ^a   Gaskell, Sean N ^a   Elsegood, Mark R J ^a   Martin, William P ^b  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

HARMICINE; INDOLE ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 34447290697     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.034     Document Type: Article

References (21)

1. World Health Organization: www.who.int/leishmaniasis/en/.
2. Kam T.-S., and Sim K.-M. Phytochemistry 47 (1998) 145-147
3. Knolker H.-J., and Agarwal S. Synlett (2004) 1767-1768
4. Itoh T., Miyazaki M., Nagata K., Yokoya M., Nakamura S., and Ohsawa A. Heterocycles 58 (2002) 115-118
5. Itoh T., Miyazaki M., Nagata K., Yokoya M., Nakamura S., and Ohsawa A. Heterocycles 63 (2004) 655-661
6. Allin S.M., Khera J.S., Witherington J., and Elsegood M.R.J. Tetrahedron Lett. 47 (2006) 5737-5739
7. Allin S.M., Duffy L.J., Page P.C.B., McKee V., Edgar M., McKenzie M.J., Amat M., Bassas O., Santos M.M.M., and Bosch J. Tetrahedron Lett. 47 (2006) 5713-5716
8. Allin S.M., Khera J.S., Thomas C.I., Witherington J., Doyle K., Elsegood M.R.J., and Edgar M. Tetrahedron Lett. 47 (2006) 1961-1964
9. Allin S.M., Thomas C.I., Allard J.E., Doyle K., and Elsegood M.R.J. Eur. J. Org. Chem. (2005) 4179-4186
10. Allin S.M., Thomas C.I., Doyle K., and Elsegood M.R.J. J. Org. Chem. 70 (2005) 357-359
11. Allin S.M., Streetley G.B., Slater M., James S.L., and Martin W.P. Tetrahedron Lett. 45 (2004) 5493-5496
12. Allin S.M., Thomas C.I., Allard J.E., Doyle K., and Elsegood M.R.J. Tetrahedron Lett. 45 (2004) 7103-7105
13. Allin S.M., Thomas C.I., Allard J.E., Duncton M., Elsegood M.R.J., and Edgar M. Tetrahedron Lett. 44 (2003) 2335-2337
14. Allin S.M., James S.L., Elsegood M.R.J., and Martin W.P. J. Org. Chem. 67 (2002) 9464-9467
15. Allin S.M., Vaidya D.G., James S.L., Allard J.E., Smith T.A.D., McKee V., and Martin W.P. Tetrahedron Lett. 43 (2002) 3661-3663
16. Allin S.M., James S.L., Martin W.P., Smith T.A.D., and Elsegood M.R.J. J. Chem. Soc., Perkin Trans. 1 (2001) 3029-3036
17. Allin S.M., James S.L., Martin W.P., and Smith T.A.D. Tetrahedron Lett. 41 (2001) 3943-3946
18. Allin S.M., Northfield C.J., Page M.I., and Slawin A.M.Z. Tetrahedron Lett. 39 (1998) 4905-4908
19. Crystallographic data (excluding structure factors) for structure 3 (R = 0.0464) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 641155. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
20. 2 requires 212.1181).
21. Szawkalo J., Czarnocki S.J., Zawadzka A., Wojtasiewicz K., Leniewski A., Maurin J.K., Czarnocki Z., and Drabowicz J. Tetrahedron: Asymmetry 18 (2007) 406-413