Tandem radical cyclization-based strategy for the synthesis of oxa- and aza-cages: a case of fragmentation versus cyclization

Tetrahedron Letters

Volumn 51, Issue 25, 2010, Pages 3324-3329

  Gharpure, Santosh J ^a   Porwal, Suheel K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONIC ACID; ESTER; ETHER DERIVATIVE; IODIDE; KETONE DERIVATIVE; RADICAL;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; FRAGMENTATION REACTION; MOLECULE; STEREOCHEMISTRY; SYNTHESIS;

EID: 77953139080     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.081     Document Type: Article

References (66)

1. For reviews, see:. Eaton P.E. Angew. Chem., Int. Ed. Engl. 31 (1992) 1421
2. Griffin G.W., and Marchand A.P. Chem. Rev. 89 (1989) 997
3. Marchand A.P. Chem. Rev. 89 (1989) 1011
4. Paquette L.A. Chem. Rev. 89 (1989) 1051
5. Klunder A.J.H., and Zwanenburg B. Chem. Rev. 89 (1989) 1035
6. Osawa E., and Yonemitsu O. Carbocyclic Cage Compounds (1992), VCH, New York
7. Olah G.A. Cage Hydrocarbons (1990), Wiley, New York
8. Mehta G., and Vidya R. J. Org. Chem. 66 (2001) 6905 and references therein
9. Geldenhuys W.J., Malan S.F., Murugesan T., Van der Schyf C.J., and Bloomquist J.R. Bioorg. Med. Chem. 12 (2004) 1799
10. Mdzinarishvili A., Geldenhuys W.J., Abbruscato T.J., Bickel U., Klein J., and Van der Schyf C. Neurosci. Lett. 383 (2005) 49
11. Janin Y.L. Bioorg. Med. Chem. 15 (2007) 2479
12. James B., Suresh E., and Nair M.S. Synlett (2006) 3479
13. Khan F.A., Dwivedi V., and Rout B. Tetrahedron Lett. 48 (2007) 207
14. Carrenfo M.C., Luzon C.G., and Ribagorda M. Chem. Eur. J. 8 (2002) 208
15. Marchand A.P., Kumar V.S., and Hariprakasha H.K. J. Org. Chem. 66 (2001) 2072
16. Khan F.A., and Upadhyay S.K. Tetrahedron Lett. 49 (2008) 6111
17. Kong N.-C., Zhang Y., Gao S., Lu Y., Zheng Q.-T., Sun Q.-Y., Yang F.-M., Di Y.-T., and Hao X.-J. Tetrahedron Lett. 50 (2009) 957 and references therein
18. Mehta G., Gagliardini V., Schaefer C., and Gleiter R. Org. Lett. 6 (2004) 1617
19. Mehta G., and Vidya R. J. Org. Chem. 66 (2001) 6913
20. Mehta G., and Vidya R. J. Org. Chem. 65 (2000) 3497
21. Mehta G., Vidya R., Sharma P.K., and Jemmis E.D. Tetrahedron Lett. 41 (2000) 2999
22. Mehta G., Vidya R., and Venkatesan K. Tetrahedron Lett. 40 (1999) 2417
23. Mehta G., and Vidya R. Tetrahedron Lett. 39 (1998) 6403
24. Mehta G., and Uma R. Chem. Commun. (1998) 1735
25. Mehta G., and Vidya R. Tetrahedron Lett. 38 (1997) 4177
26. Mehta G., and Vidya R. Tetrahedron Lett. 38 (1997) 4173
27. Wu C.Y., Lin H.C., Wang Z., and Wu H.J. J. Org. Chem. 66 (2001) 4610
28. Wu H.J., Chao C.S., and Lin C.C. J. Org. Chem. 63 (1998) 7687
29. Wu H.J., and Lin C.C. J. Org. Chem. 60 (1995) 7558
30. Wu H.J., and Lin C.C. J. Org. Chem. 61 (1996) 3820
31. Wu H.J., and Wu C.Y. J. Org. Chem. 64 (1999) 1576
32. Wu H.J., and Chern J.H. J. Org. Chem. 62 (1997) 3208
33. Wu H.J., and Chern J.H. Chem. Commun. (1997) 547
34. Lin H.C., Wu C.Y., and Wu H.J. J. Chin. Chem. Soc. 44 (1997) 609 and references therein
35. Prinzbach H., and Klaus M. Angew. Chem., Int. Ed. Engl. 8 (1969) 276
36. Marchand A.P., Reddy G.M., Watson W.H., and Kashyap R. Tetrahedron 46 (1990) 3409
37. Sasaki T., Eguchi S., Kiriyama T., and Hiroaki O. Tetrahedron 30 (1974) 2707
38. Singh P. J. Org. Chem. 44 (1979) 843
39. Coxon J.M., Fong S.T., McDonald D.Q., O'Connell M.J., and Steel P.J. Tetrahedron Lett. 32 (1991) 7115
40. Suri S.C. J. Org. Chem. 58 (1993) 4153
41. Mehta G., Srikrishna A., Reddy A.V., and Nair M.S. Tetrahedron 37 (1981) 4543
42. Mehta G., and Nair M.S. J. Am. Chem. Soc. 107 (1985) 7519
43. Marchand A.P., LaRoe W.D., Sharma G.V.M., Suri S.C., and Reddy D.S. J. Org. Chem. 51 (1986) 1622
44. Fessner W.D., and Prinzbach H. Tetrahedron 42 (1986) 1797
45. Smith E.C., and Barborak J.C. J. Org. Chem. 41 (1976) 1433
46. Marchand A.P., and Chou T.C. Tetrahedron 31 (1975) 2655
47. Mehta G., and Reddy K.R. J. Org. Chem. 52 (1987) 460
48. Mehta G., and Rao H.S.P. J. Chem. Soc., Chem. Commun. (1986) 472
49. Mehta G., Rao H.S.P., and Reddy K.R. J. Chem. Soc., Chem. Commun. (1987) 78
50. For some excellent reviews, see:. McCarroll A.J., and Walton J.C. Angew. Chem., Int. Ed. 40 (2001) 2224
51. McCarroll A., and Walton J.C. J. Chem. Soc., Perkin Trans. 1 (2001) 3215
52. Yet L. Tetrahedron 55 (1999) 9349
53. Malacria M. Chem. Rev. 96 (1996) 289
54. Giese B. In: Renaud P., and Sibi M.P. (Eds). Radicals in Organic Synthesis (2001), Wiley-VCH, Weinheim 381-399
55. Gharpure S.J., and Porwal S.K. Synlett (2008) 242
56. Gharpure S.J., and Porwal S.K. Tetrahedron Lett. 50 (2009) 7162
57. Gharpure S.J., and Reddy S.R.B. Org. Lett. 11 (2009) 2519
58. Gharpure S.J., Shukla M.K., and Vijayasree U. Org. Lett. 11 (2009) 5466
59. 3SnH (136 μL, 0.51 mmol) and AIBN (8.5 mg, 0.05 mmol) in dry benzene (10 mL) over a period of 2 h under nitrogen atmosphere. The reaction mixture was further refluxed till completion (ca. 3 h, TLC control). It was then cooled and the solvent was removed under reduced pressure. Purification of the residue by silica gel column chromatography using ethyl acetate/hexanes (1:15) as eluent furnished the oxa-cage 3ba (40.0 mg, 69%) as a white solid.
60. 3) δ 7.19 (d, J = 7.3 Hz, 1H), 7.12 (t, J = 7.6 Hz, 1H), 6.85 (t, J = 7.3 Hz, 1H), 6.74 (d, J = 8.0 Hz, 1H), 5.05 (dd, J = 10.3, 3.7 Hz, 1H), 4.98 (s, 1H), 4.86 (s, 1H), 3.76 (dd, J = 8.7, 3.0 Hz, 1H), 3.65 (dd, J = 10.6, 4.2 Hz, 1H), 3.65-3.60 (m, 2H), 2.79 (t, J = 3.5 Hz, 1H), 2.75-2.60 (m, 3H), 2.54 (q, J = 4.0 Hz, 1H), 2.35 (ddd, J = 12.9, 10.3, 6.5 Hz, 1H)
61. For some selected examples for fragmentation reactions using radicals, see:. Tsang R., and Fraser-Reid B. J. Am. Chem. Soc. 108 (1986) 8102
62. Nishida A., Takahashi H., Takeda H., Takada N., and Yonemitsu O. J. Am. Chem. Soc. 112 (1990) 902
63. Beckwith A.L.J., O'Shea D.M., and Westwood S.W. J. Am. Chem. Soc. 110 (1988) 2565
64. Dowd P., and Choi S.-C. J. Am. Chem. Soc. 109 (1987) 6548
65. Mehta G., and Singh V. Chem. Rev. 99 (1999) 881 and references therein
66. 3; unit cell parameters: a 22.783(3) b 6.4262(8) c 19.301(2) beta 116.444(5) space group C2/c; CCDC No. 770582. CCDC 770582 contains the supplementary crystallographic data for this Letter. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif.