A concise and enantioselective approach to the total synthesis of (-)-lasubine I

Tetrahedron Letters

Volumn 47, Issue 44, 2006, Pages 7681-7684

  Liu, Shengyang ^a   Fan, Yuping ^b   Peng, Xinxiang ^b   Wang, Wei ^c,d   Hua, Weiyi ^a   Akber, Haji ^b   Liao, Lixin ^b,e  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^d UNIVERSITY OF NEW MEXICO   (United States)

^e SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Lasubine; Quinolizidine; Ring closing metathesis; Roush allylboration

Indexed keywords

ALKALOID; LASUBINE 1; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; RING CLOSING METATHESIS;

EID: 33749128100     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.137     Document Type: Article

References (51)

1. For reviews, see:. Golebiewski W.M., and Wróbel J.T. In: Rodrigo R.G.A. (Ed). The Alkaloids: Chemistry and Physiology Vol. 18 (1981), Academic, New York 263
2. Fuji K. The Alkaloids Vol. 35 (1989), Academic Press, New York Chapter 3, p 155
3. Michael J.P. Nat. Prod. Rep. (1993) 51
4. Michael J.P. Nat. Prod. Rep. 14 (1997) 21
5. Mitchinson A., and Nadin A. J. Chem. Soc., Perkin Trans. 1 (2000) 2862
6. Fuji K., Yamada T., Fujita E., and Murata H. Chem. Pharm. Bull. 26 (1978) 2515 and physical data for the synthesized (-)-lasubine I see Supplementary data
7. For the racemic syntheses of lasubine I, see: Ref. 1 and. Iida H., Tanaka M., and Kibayashi C. J. Chem. Soc., Chem. Commun. (1983) 1143
8. Iida H., Tanaka M., and Kibayashi C. J. Org. Chem. 49 (1984) 1909
9. Ent H., De Koning H., and Speckamp W.N. Heterocycles 27 (1988) 237
10. Beckwith A.L.J., Joseph S.P., and Mayadunne R.T.A. J. Org. Chem. 58 (1993) 4198
11. Bardot V., Gardette D., Gelas-Mialhe Y., Gramain J.-C., and Remuson R. Heterocycles 48 (1998) 507
12. For enantioselective syntheses of (-)-lasubine I, see:. Comins D.L., and LaMunyon D.H. J. Org. Chem. 57 (1992) 5807
13. Chalard P., Remuson R., Gelas-Mialhe Y., and Gramain J.-C. Tetrahedron: Asymmetry 9 (1998) 4361
14. Ratni H., and Kuendig E.P. Org. Lett. 1 (1999) 1997
15. Davis F.A., Rao A., and Carroll P.J. Org. Lett. 5 (2003) 3855
16. For the racemic syntheses of lasubine II, see: Ref. 1 and. Narasaka K., Yamazaki S., and Ukaji Y. Chem. Lett. (1985) 1177
17. Hoffmann R.W., and Endesfelder A. Liebigs Ann. Chem. (1986) 1823
18. Narasaka K., Ukaji Y., and Yamazaki S. Bull. Chem. Soc. Jpn. 59 (1986) 525
19. Brown J.D., Foley M.A., and Comins D.L. J. Am. Chem. Soc. 110 (1988) 7445
20. Pilli R.A., Dias L.C., and Maldaner A.O. Tetrahedron Lett. 34 (1993) 2729
21. Pilli R.A., Dias L.C., and Maldaner A.O. J. Org. Chem. 60 (1995) 717
22. For enantioselective syntheses of (-)-lasubine II, see:. Ukaji Y., Ima M., Yamada T., and Inomata K. Heterocycles 52 (2000) 563
23. Davis F.A., and Chao B. Org. Lett. 2 (2000) 2623
24. Ma D., and Zhu W. Org. Lett. 3 (2001) 3927
25. Back T.G., and Hamilton M.D. Org. Lett. 4 (2002) 1779
26. Gracias V., Zeng Y., Desai P., and Aubé J. Org. Lett. 5 (2003) 4999
27. Zaja M., and Blechert S. Tetrahedron 60 (2004) 9629
28. Back T.G., Hamilton M.D., Lim V.J.J., and Parvez M. J. Org. Chem. 70 (2005) 967
29. Fu G.C., Maguyen S.T., and Grubbs R.H. J. Am. Chem. Soc. 115 (1993) 9856
30. For recent reviews using RCM for synthesis of alkaloids, see:. Brenneman J.B., and Martin S.F. Curr. Org. Chem. 9 (2005) 1535
31. Martin S.F. Pure Appl. Chem. 77 (2005) 1207
32. For recent selected examples for ring-closing metathesis, see:. Hong S.H., and Grubbs R.H. J. Am. Chem. Soc. 128 (2006) 3508
33. Lee A.-L., Malcolmson S.J., Puglisi A., Schrock R.R., and Hoveyda A.H. J. Am. Chem. Soc. 128 (2006) 5153
34. Smith III A.B., Mesaros E.F., and Meyer E.A. J. Am. Chem. Soc. 128 (2006) 5292
35. Liu Z., and Rainier J.D. Org. Lett. 8 (2006) 459
36. BouzBouz S., and Cossy J. Tetrahedron Lett. 47 (2006) 901
37. Kim M., and Lee D. J. Am. Chem. Soc. 127 (2005) 18024
38. Crimmins M.T., Zuccarello J.L., Cleary P.A., and Parrish J.D. Org. Lett. 8 (2006) 159
39. Maechling S., Zaja M., and Blechert S. Adv. Synth. Catal. 347 (2005) 1413
40. Kummer D.A., Brenneman J.B., and Martin S.F. Org. Lett. 7 (2005) 4621
41. Stoianova D.S., Whitehead A., and Hanson P.R. J. Org. Chem. 70 (2005) 5880
42. Yao Q.W., and Zhang Y.L. J. Am. Chem. Soc. 126 (2004) 74
43. Roush W.R., Ratz A.M., and Joblonowski J.A. J. Org. Chem. 57 (1992) 2047
44. Hoong L.K., Palmer M.A., Park J.C., and Roush W.R. J. Org. Chem. 55 (1990) 4109
45. Hoong L.K., Palmer M.A., Park J.C., Palkowitz A.D., and Roush W.R. J. Org. Chem. 55 (1990) 4117
46. Sivakumar A.V., Babu G.S., and Bhat S.V. Tetrahedron: Asymmetry 12 (2001) 1095
47. R = 20.52 min (major), 97% ee.
48. Amberg W., Bennani Y.L., Chadha R.K., Crispino G.A., Davis W.D., Hartung J., Jeong K.-S., Ogino Y., Shibata T., and Sharpless K.B. J. Org. Chem. 58 (1993) 844
49. Zhong Y.L., and Shing T.K.M. J. Org. Chem. 62 (1997) 2622
50. Kim Y.-H., and Choi J.-Y. Tetrahedron Lett. 37 (1996) 5543
51. McIntosh J.M., and Matassa L.C. J. Org. Chem. 62 (1997) 2622