Cascade and RCM syntheses of chiral tricyclic alkaloids from (S)-1,2,3,4-tetrahydro isoquinoline carboxylic acid

Tetrahedron Asymmetry

Volumn 20, Issue 10, 2009, Pages 1154-1159

  Muroni, Daniele ^a   Mucedda, Mauro ^a   Saba, Antonio ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

10,10A DIHYDRO 5H PYRROLO[1,2 B]ISOQUINOLIN 3 ONE; 11,11A,3 TRIHYDRO 6H PYRIDINO[1,2 B]ISOQUINOLIN 4 ONE; 2 [1 OXO 3 BUTENYL] 3 VINYL 3,4 DIHYDROISOQUINOLIN 2(1H) YL; 2 [1 OXO 4 PENTENYL] 3 VINYL 3,4 DIHYDROISOQUINOLIN 2(1H) YL; 2 [1 OXO PROPENYL] 3 VINYL 3,4 DIHYDROISOQUINOLIN 2(1H) YL; 3,4,12,12A TETRAHYDRO 7H AZEPINO[1,2B]ISOQUINOLIN 5 ONE; ALKALOID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 66149176802     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.04.003     Document Type: Article

References (51)

1. Thurston D.E., and Bose D.S. Chem. Rev. 94 (1994) 433
2. Takahata H., and Momose T. In: Cordell G.A. (Ed). The Alkaloids Chemistry and Pharmacology (1993), Academic Press, San Diego
3. Saba A. Tetrahedron Lett. 44 (2003) 2895
4. Muroni D., Saba A., and Culeddu N. Tetrahedron: Asymmetry 15 (2004) 2609
5. Muroni D., Saba A., and Culeddu N. Tetrahedron 62 (2006) 1459
6. Muroni D., Saba A., and Culeddu N. Heterocycles 68 (2006) 47
7. Mucedda M., Muroni D., Saba A., and Manassero C. Tetrahedron 63 (2007) 12232
8. Mucedda M., Muroni D., and Saba A. Heterocycles 78 (2009) 635
9. Muroni D., Mucedda M., and Saba A. Tetrahedron Lett. 49 (2008) 2373
10. Padwa A., and Weingarten M.D. Chem. Rev. 96 (1996) 223
11. For a review of the Stevens [1,2]-rearrangement of ammonium ylides, see:. Vanecko J.A., Wan H., and West F.G. Tetrahedron 61 (2005) 1043
12. For examples of [2,3]-rearrangement of allylic ammonium ylides, see:. Clark J.S., Hodgson P.B., Goldsmith M.D., Blake A.J., Cooke P.A., and Street L.J. J. Chem. Soc., Perkin Trans. 1 (2001) 3325
13. Clark J.S., and Middleton M.D. Org. Lett. 4 (2002) 765
14. Roberts E., Sancon J.P., Sweeney J.B., and Workman J.A. Org. Lett. 5 (2003) 4775
15. Zhou C.Y., Yu W.Y., Chan P.W., and Che C.M. J. Org. Chem. 69 (2004) 7072
16. For a review of ammonium ylides generated by diazo compounds, see:. Doyle M.P., McKervey M.A., and Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds (1997), John Wiley and Sons, New York, NY
17. For some examples of spiro-to-fused ammonium ylides strategy:. Curtis E.A., Padwa A., and Worsencroft K.J. Tetrahedron Lett. 38 (1997) 3319
18. Padwa A., Brodney M.A., Marino Jr. J.P., and Sheean S.M. J. Org. Chem. 62 (1997) 78
19. Padwa A., and Price A.T. J. Org. Chem. 63 (1998) 5556
20. Padwa A., Snyder J.P., Curtis E.A., Sheean S.M., Worsencroft K.J., and Kappe C.O. J. Am. Chem. Soc. 122 (2000) 8155
21. Vanecko J.A., and West F.G. Org. Lett. 4 (2002) 2813
22. West F.G., Glaeske K.W., and Naidu B.N. Synthesis (1993) 977
23. Vanecko J.A., and West F.G. Org. Lett. 7 (2005) 2949
24. Zibuck R., and Streiber J.M. J. Org. Chem. 54 (1989) 4717
25. Glaeske K.W., and West F.G. Org. Lett. 1 (1999) 31
26. Goncalves-Farbos M.-H., Vial L., and Lacour J. Chem. Commun (2008) 829 and references cited herein
27. Giannis A., and Kolter T.I. Angew. Chem., Int. Ed. Engl. 32 (1993) 1244
28. For the use of spirocyclic ammonium ylide rearrangements to prepare medium-sized azacycles, see:. Wright D.I., Weekly R.M., Groff R., and McMills M.C. Tetrahedron Lett. 37 (1996) 2165
29. Clark J.S., Hodgson P.B., Goldsmith M.D., Blake A.J., Cooke P.A., and Street L.J. J. Chem. Soc., Perkin Trans. 1 (2001) 3325
30. Molander G.A., and Romero J.A.C. Tetrahedron 61 (2005) 2631
31. 3): δ = 5.67, J = 8.1, 3.9 Hz (-HC{double bond, long}CH from selective decoupling).
32. Blid J., Pankin O., and Somfai P. J. Am. Chem. Soc. 127 (2005) 9352
33. Kaiser G.W., Ashbrook C.W., and Baldwin J.E. J. Am. Chem. Soc. 93 (1971) 2342
34. Hiroi K., and Nakazawa K. Chem. Lett. (1980) 1077
35. Clark J.S., and Hodgson P.B. Tetrahedron Lett. 36 (1995) 2519
36. Gawley R.E., Zhang Q., and Campagna S. J. Am. Chem. Soc. 117 (1995) 11817
37. Glaeske K.W., and West F.G. Org. Lett. 1 (1999) 31
38. Aggarwal V.K., Fang G., Charmant J.P.H., and Meek G. Org. Lett 5 (2003) 1757
39. 1H NMR spectra to those obtained from the racemate.
40. Shamma M., and Moniot J.L. Isoquinoline Alkaloid Research (1978), Plenum Press, New York
41. Grubbs R.H., Miller S.J., and Fu G.C. Acc. Chem. Res. 28 (1995) 446
42. Grubbs R.H. Tetrahedron 60 (2004) 7117
43. Compain P. Adv. Synth. Catal. 349 (2007) 1829 Successful RCM reactions performed utilizing substrates containing secondary and tertiary amines are reported in this review
44. Kadlecikova K., Dalla V., Marchalin S., Decroix B., and Baran P. Tetrahedron 61 (2005) 4743
45. Carpes M.J.S., Miranda P.C.M.L., and Correira C.R.D. Tetrahedron Lett. 38 (1997) 1879
46. Cotton N.R., Johnstone A.N.C., and North M. Tetrahedron 51 (1995) 8525
47. Baldwin J.E., Adlington R.M., and Gollins D.W. Tetrahedron 51 (1995) 5169
48. Sasaki N.A., Pauly R., Fontaine C., Chiaroni A., Riche C., and Potier P. Tetrahedron Lett. 35 (1994) 241
49. West F.G., and Naidu B.N. J. Org. Chem. 59 (1994) 6051
50. Cativela C., and Diaz de Villegas M.D. Tetrahedron: Asymmetry 9 (1998) 3517
51. Hanessian S., McNaughton-Smith G., Lombard H.G., and Lubell W.D. Tetrahedron 53 (1997) 12789