A conjugate addition/dipolar-cycloaddition cascade sequence for the synthesis of (±)-cylindricine C

Tetrahedron

Volumn 66, Issue 21, 2010, Pages 3643-3650

  Flick, Andrew C ^a   Arevalo Caballero, Maria José ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

2,3 Bis(phenylsulfonyl) 1,3 butadiene; Alkaloid; Cylindricine C; Intramolecular dipolar cycloaddition; Nitrone; Oxime

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ALKADIENE; ALKALOID; BASE; BORNANE DERIVATIVE; CYLINDRICINE C; ISOXAZOLIDINE DERIVATIVE; NITRONE; OXIME DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; CYCLOADDITION; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 77951098457     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.088     Document Type: Article

References (61)

1. Blackman A.J., Li C., Hockless D.C.R., Skelton B.W., and White A.H. Tetrahedron 49 (1993) 8645
2. Li C., and Blackman A.J. Aust. J. Chem. 48 (1995) 955
3. For an excellent review, see:. Weinreb S.M. Chem. Rev. 106 (2006) 2531
4. Werner K.M., de los Santos J.M., Weinreb S.M., and Shang M. J. Org. Chem. 64 (1999) 686
5. Li C., and Blackman A.J. Aust. J. Chem. 47 (1994) 1355
6. Biard J.F., Guyot S., Roussakis C., Verbist J.F., Vercauteren J., Weber J.F., and Boukef K. Tetrahedron Lett. 35 (1994) 2691
7. Mihara H., Shibuguchi T., Kuramochi A., Ohshima T., and Shibasaki M. Heterocycles 72 (2007) 421
8. Shibuguchi T., Mihara H., Kuramochi A., Sakuraba S., Takashi O., and Shibasaki M. Angew. Chem., Int. Ed. 45 (2006) 4635
9. Pearson W.H., and Ren Y. J. Org. Chem. 64 (1999) 688
10. Werner K.M., de los Santos J.M., Weinreb S.M., and Shang M. J. Org. Chem. 64 (1999) 4865
11. Sun P., Sun C., and Weinreb S.M. J. Org. Chem. 67 (2002) 4337
12. Greshock T.J., and Funk R.L. Org. Lett. 3 (2001) 3511
13. Abe H., Aoyagi S., and Kibayashi C. J. Am. Chem. Soc. 122 (2000) 4583
14. Abe H., Aoyagi S., and Kibayashi C. Angew Chem., Int. Ed. 41 (2002) 3017
15. Molander G.A., and Ronn M. J. Org. Chem. 64 (1999) 5183
16. Liu J.F., and Heathcock C.H. J. Org. Chem. 64 (1999) 8263
17. Trost B.M., and Rudd M.T. Org. Lett. 5 (2003) 4599
18. Arai T., Abe H., Aoyagi S., and Kibayashi C. Tetrahedron Lett. 45 (2004) 5921
19. Abe H., Aoyagi S., and Kibayashi C. J. Am. Chem. Soc. 127 (2005) 1473
20. Liu J., Hsung R.P., and Peters S.D. Org. Lett. 6 (2004) 3989
21. Liu J., Swidorski J.J., Peters S.D., and Hsung R.P. J. Org. Chem. 70 (2005) 3898
22. Wang J., Swidorski J.J., Sydorenko N., Hsung R.P., Coverdale H.A., Kuyava J.M., and Liu J. Heterocycles 70 (2006) 423
23. Swidorski J.J., Wang J., and Hsung R.P. Org. Lett. 8 (2006) 777
24. Canesi S., Bouchu D., and Ciufolini M.A. Angew. Chem., Int. Ed. 43 (2004) 4336
25. Padwa A., and Norman B.H. Tetrahedron Lett. 29 (1988) 2417
26. Norman B.H., Gareau Y., and Padwa A. J. Org. Chem. 56 (1991) 2154
27. For a preliminary report dealing with the synthesis of cyclindricine C, see:. Flick A.C., Caballero M.J.A., and Padwa A. Org. Lett. 10 (2008) 1871
28. Padwa A., Watterson S.H., and Ni Z. Org. Synth. 74 (1997) 147
29. Stearman C.J., Wilson M.S., and Padwa A. J. Org. Chem. 74 (2009) 3491
30. Wilson M.S., and Padwa A. J. Org. Chem. 73 (2008) 9601
31. Smith A.B., Hale K.J., and McCauley J.P. Tetrahedron Lett. 30 (1989) 5579
32. Comins D.L., and Al-awar R.S. J. Org. Chem. 60 (1995) 711
33. Brewster J.H., Patterson J., and Fidler D.A. J. Am. Chem. Soc. 76 (1954) 6368
34. Brewster J.H. J. Am. Chem. Soc. 76 (1954) 6364
35. Terry T.J., Dubois G., Murphy A., and Stack T.D.P. Angew. Chem., Int. Ed. 46 (2007) 945
36. Murphy A., and Stack T.D.P. J. Mol. Catal. A 251 (2006) 78
37. Murphy A., Pace A., and Stack T.D.P. Org. Lett. 6 (2004) 3119
38. Dubois G., Murphy A., and Stack T.D.P. Org. Lett. 5 (2003) 2469
39. Murphy A., Dubois G., and Stack T.D.P. J. Am. Chem. Soc. 125 (2003) 5250
40. The low yield of 36 can be attributed to the recovery of a substantial amount of the endo-starting alkene 28 as well as some decomposition products derived from a N-oxide intermediate.
41. White J.D., and Hansen J.D. J. Org. Chem. 70 (2005) 1963
42. Several examples of amplified nitrogen nucleophilicity under reductive conditions have been reported in the literature, particularly with substrates that bear a tethered electrophile. For some select cases, see:
43. Pearson W.H., and Hines J.V. J. Org. Chem. 65 (2000) 5785
44. Denmark S.E., and Martinborough E.A. J. Am. Chem. Soc. 121 (1999) 3046
45. Martin S.F., Chen H.J., and Yang C.-P. J. Org. Chem. 58 (1993) 2876
46. Martin S.F., Chen H.J., and Lynch V.M. J. Org. Chem. 60 (1995) 276
47. Smith III A.B., and Kim D.S. Org. Lett. 6 (2004) 1493
48. Smith III A.B., and Kim D.S. Org. Lett. 7 (2005) 3247
49. Smith III A.B., and Kim D.S. J. Org. Chem. 71 (2006) 2547
50. Vite G.D., and Spencer T.A. J. Org. Chem. 53 (1988) 2555
51. Conia J.M., and Rouessac F. Tetrahedron 16 (1961) 45
52. One of the reviewers has suggested from modeling studies at the AM1 level that the enolate anion of 28 reacts with the electrophile on the concave face so that the alkylation proceeds directly to compound 30.
53. Leonard N.J., Hay A.S., Fulmer R.W., and Gash V.W. J. Am. Chem. Soc. 77 (1955) 439
54. Leonard N.J., and Hauck F.P. J. Am. Chem. Soc. 79 (1957) 5279
55. Leonard N.J., and Cook A.G. J. Am. Chem. Soc. 81 (1959) 5627
56. Leonard N.J., and Musker W.K. J. Am. Chem. Soc. 81 (1959) 5631
57. Möhrle H., and Claas M. Pharmazie 43 (1988) 749
58. Brown J.D., Foley M.A., and Comins D.L. J. Am. Chem. Soc. 110 (1988) 7445
59. Comins D.L., and Dehghani A. J. Org. Chem. 60 (1995) 794
60. Donohoe T.J., Johnson D.J., Mace L.H., Bamford M.J., and Ichihara O. Org. Lett. 7 (2005) 435
61. Molander G.A., McWilliams J.C., and Noll B.C. J. Am. Chem. Soc. 119 (1997) 1265