Total synthesis of the lupin alkaloid cytisine: comparison of synthetic strategies and routes

Tetrahedron

Volumn 63, Issue 9, 2007, Pages 1885-1897

  Stead, Darren ^a   O'Brien, Peter ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Alkaloids; Bispidines; Cytisine; Pyridones; Total synthesis

Indexed keywords

CYTISINE; DIPYRONE; GLUTARIMIDE; PIPERIDINE; PYRIDINE; PYRIDONE DERIVATIVE; VARENICLINE;

BENZYLATION; CYCLIZATION; DRUG ACTIVITY; DRUG SYNTHESIS; HYDROGENATION; HYDROLYSIS; NONHUMAN; OXIDATION; PRIORITY JOURNAL; REVIEW; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

DRYOBALANOPS;

EID: 33846543653     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.10.017     Document Type: Review

References (45)

1. Leonard N.J. The Alkaloids Vol. III (1953), Academic, New York, NY p 120
2. Husemann, and Marmé. Edin. Med. J. 7 (1862) 1025
3. Partheil. Arch. Pharm. 232 (1894) 167
4. Freund. Ber. 34 (1901) 605
5. Späth. Montash 40 (1919) 93
6. Ewins. J. Chem. Soc. 133 (1913) 97
7. Ing H.R. J. Chem. Soc. (1932) 2778
8. Ing H.R. J. Chem. Soc. (1931) 2195
9. Lecoq H. Bull. Soc. Chim. Fr. (1943) 153
10. El-Shazly A., Sarg T., Atcya A., Aziz E.A., Witte L., and Wink M. Pharmazie 51 (1996) 768
11. Marrière M., Rouden J., Tadino V., and Lasne M.-C. Org. Lett. 2 (2000) 1121
12. Dixon A.J., McGrath M.J., and O'Brien P. Org. Synth. 83 (2006) 141
13. For a recent overview of nicotinic pharmacology relevant to cytisine, see:
14. Holladay M.W., Dart M.J., and Lynch J.K. J. Med. Chem. 40 (1997) 4169
15. Jensen A.A., Frolund B., Lijefors T., and Krogsgaard-Larsen P. J. Med. Chem. 48 (2005) 4705
16. Canu Boido C., and Sparatore F. Farmaco 54 (1999) 438
17. Nicolotti O., Canu Boido C., Sparatore F., and Carotti A. Farmaco 57 (2002) 469
18. Canu Boido C., Tasso B., Boido V., and Sparatore F. Farmaco 58 (2003) 265
19. Coe J.W., Brooks P.R., Vetelino M.G., Wirtz M.C., Arnold E.P., Huang J., Sands S.B., Davis T.I., Lebel L.A., Fox C.B., Shrikhande A., Heym J.H., Schaeffer E., Rollema H., Lu Y., Mansbach S., Chambers L.K., Rovetti C.C., Schulz D.W., Tingley F.D., and O'Neill B.T. J. Med. Chem. 48 (2005) 3474
20. Coe J.W., Vetelino M.G., Bashore C.G., Wirtz M.C., Brokks P.R., Arnold E.P., Lebel L.A., Fox C.A., Sands S.B., Davis T.I., Schulz D.W., Rollema H., Tingley F.D., and O'Neill B.T. Bioorg. Med. Chem. Lett. 15 (2005) 2974
21. Chellappan S.K., Xiao Y., Tueckmantel W., Kellar K.J., and Kozikowski A.P. J. Med. Chem. 49 (2006) 2673
22. Quinn D.I., Wodak A., and Day R.O. Clin. Pharmacokinet. 33 (1997) 344
23. Scharfenberg G., Benndorf S., and Kempe G. Dtsch. Gesundheitsw. 26 (1971) 463
24. Barlow R.B., and McLead L.J. J. Pharmacol. 35 (1969) 161
25. Reavill C., Walther B., Stolerman I.P., and Testa B. Neuropharmacology 29 (1990) 619
26. van Tamelen E.E., and Baren J.S. J. Am. Chem. Soc. 77 (1955) 4944
27. van Tamelen E.E., and Baran J.S. J. Am. Chem. Soc. 80 (1958) 4659
28. Bohlmann F., Englisch A., Ottawa N., Sander H., and Weise W. Chem. Ber. 89 (1956) 792
29. Govindachari T.R., Rajadurai S., Subramanian M., and Thyagarajan B.S. J. Chem. Soc. (1957) 3839
30. O'Neill B.T., Yohannes D., Bundesmann M.W., and Arnold E.P. Org. Lett. 2 (2000) 4201
31. Coe J.W. Org. Lett. 2 (2000) 4205
32. Botuha C., Galley C.M.S., and Gallagher T. Org. Biomol. Chem. 2 (2004) 1825
33. Stead D., O'Brien P., and Sanderson A.J. Org. Lett. 7 (2005) 4459
34. Danieli B., Lesma G., Passarella D., Sacchetti A., Silvani A., and Virdis A. Org. Lett. 6 (2004) 493
35. Honda T., Takahashi R., and Namiki H. J. Org. Chem. 70 (2005) 499
36. Gray D., and Gallagher T. Angew. Chem., Int. Ed. 45 (2006) 2419
37. Nshimyumkiza P., Cahard D., Rouden J., Lasne M.-C., and Paquevent J.-C. Tetrahedron Lett. 42 (2001) 7787
38. Murakoshi I., Kidoguchi E., Haginiwa J., Phmiya S., Higashiyama K., and Otomasu H. Phytochemistry 20 (1981) 1407
39. Máximo P., and Lourenço A. J. Nat. Prod. 63 (2000) 201
40. Cook G.R., Beholz L.G., and Stille J.R. J. Org. Chem. 59 (1994) 3575
41. Bohlmann F., Ottawa N., and Keller R. Liebigs Ann. Chem. 587 (1954) 162
42. Bohlmann F., Englisch A., Politt J., Sander H., and Weise W. Chem. Ber. 88 (1955) 1831
43. Danieli D., Lesma G., Passarella D., and Silvani A. Synth. Commun. 27 (1997) 69
44. Danieli D., Lesma G., Passarella D., and Silvani A. Tetrahedron: Asymmetry 7 (1996) 345
45. Danieli D., Lesma G., Passarella D., and Silvani A. J. Org. Chem. 63 (1998) 3492