Synthesis of pterocarpans by means of a "Disfavored" 5-endo-trig radical cyclization reaction

European Journal of Organic Chemistry

Volumn , Issue 18, 2001, Pages 3461-3466

  Santhosh, Kalpathy Chidambareswaran ^a   Gopalsamy, Ariamala ^a   Balasubramanian, Kalputtu Kuppuswamy ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

Cyclizations; Heterocycles; Natural products; Radical reactions; Reaction mechanisms

Indexed keywords

BENZENE; CHROMENE DERIVATIVE; DEUTERIUM; ETHER DERIVATIVE; PTEROCARPAN DERIVATIVE; TRIBUTYLTIN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; ISOTOPE LABELING; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034811860     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200109)2001:18<3461::aid-ejoc3461>3.0.co;2-9     Document Type: Article

References (58)

1. [1a] D. P. Curran, in Comprehensive Organic Synthesis (Eds. B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, Elmsford, New York, 1991, vol. 4, p. 715 and 779.
2. [1b] B. Giese, in Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds Pergamon Press, Oxford, 1986.
3. [1c] W. B. Motherwell, D. Crich, Free Radical Chain Reactions in Organic Synthesis Academic Press, New York, 1992.
4. [1d] J. Fossey, D. Lefort, J. Sorba, Free Radicals in Organic Chemistry, John Wiley & Sons, New York, 1995.
5. [2a] A. L. J. Beckwith, Tetrahedron 1981, 37, 3073.
6. [2b] M. Ramaiah, Tetrahedron 1987, 43, 3541.
7. [2c] D. P. Curran, Synthesis 1988, 417 (part 1),
8. D. P. Curran, Synthesis 489 (part 2).
9. [2d] D. P. Curran, Synlett 1991, 63.
10. [2e] B. Giese, Angew. Chem. Int. Ed. Engl. 1985, 24, 553.
11. [2f] D. P. Curran, C. P. Jasperse, T. L. Fevig, Chem. Rev. 1991, 91, 1237.
12. [2g] P. Dowed, W. Zang, Chem. Rev. 1993, 93, 2091.
13. [3a] P. M. Derwick, in The Flavonoids, Advances in Research Since 1986 (Ed.: J. B. Harborne), Chapman and Hall, London, 1994, p. 166-178.
14. [3b] F. M. Dean, The Total Synthesis of Natural Products (Ed.: J. Apsimon), John Wiley & Sons, New York, 1977, vol. 1.
15. [3c] D. Gross, in Progress in the Chemistry of Organic Natural Products (Eds.: W. Herz, H. Grisebach, G. W. Kirby), Springer-Verlag, New York, 1977, vol. 34, p. 187.
16. [3d] J. L. Ingham, in Progress in the Chemistry of Organic Natural Products (Eds.: W. Herz, H. Grisebach, G. W. Kirby), Springer-Verlag, New York, 1983, vol. 43, pp. 1.
17. [3e] V. S. Kamat, F. Y. Chuo, I. Kubu, K. Nakanishi, Heterocycles 1981, 15, 1163.
18. [3f] M. Nakagawa, K. Nakanishi, L. L. Drako, J. A. Vick, Tetrahedron Lett. 1982, 23, 3855.
19. [3g] R. Kojima, S. Fukushima, A. Ueno, Y. Saiki, Chem. Pharm. Bull. 1970, 18, 2555.
20. [4a] A. C. Jain, D. K. Tuli, J. Sci. Ind. Res. 1978, 87, 287.
21. [4b] A. V. K. Prasad, R. S. Kapil, S. P. Popli, J. Chem. Soc., Perkin Trans. 1 1986, 1561.
22. [4c] S. E. N. Mohamed, P. Thomas, D. A. Whiting, J. Chem. Soc., Perkin Trans. 1 1987, 431.
23. [4d] K. Mori, H. Kisida, Liebigs Ann. Chem. 1988, 721.
24. [4e] J. C. Breytenbach, G. J. H. Rall, D. G. Roux, J. Chem. Soc., Perkin Trans. 1 1981, 2604.
25. [4f] G. N. Bidhendi, N. R Bannerji, Indian J. Chem. 1990, 29B, 366.
26. [4g] D. D. Narkhede, P. R. Iyer, C. S. R. Iyer, Tetrahedron 1990, 46, 2031.
27. [4h] A. L. Coelho, M. L. A. A. Vasconcellos, A. B. C. Simas, J. A. Rabi, P. R. R. Costa, Synthesis 1992, 914.
28. [4i] Y. Ozaki, K. Mochida, S. W. Kim, J. Chem. Soc., Chem. Commun. 1988, 374.
29. [4j] T. A. Engler, J. P. Reddy, K. D. Combrink, D. V. Velde, J. Org. Chem. 1990, 55, 1248.
30. [4k] T. A. Engler, M. A. Letavic, J. P. Reddy, J. Am. Chem. Soc. 1991, 113, 5068.
31. [4l] K. Subbaraj, M.G. Murugesh, G. K. Trivedi, J. Chem. Soc.; Perkin Trans. 1 1997, 1875.
32. [4m] T. G. Van Aardt, P. S. Van Heerden, D. Ferreira, Tetrahedron Lett. 1998, 39, 3881.
33. [4n] T. G. Van Aardt, H. Van Rensburg, D. Ferreira, Tetrahedron 1999, 55, 11773.
34. For the preliminary communication: G. Ariamala, K. K. Balasubramanian, J. Chem. Soc., Chem. Commun. 1988, 28.
35. I. Iwai, J. Ide, J. Chem. Pharm. Bull. Jpn. 1963, 11, 1042.
36. U. Rao, K. K. Balasubramanian, Tetrahedron Lett. 1983, 24, 5023.
37. D. R. Dalton, V. P. Dutta, D. C. Jones, J. Am. Chem. Soc. 1968, 90, 5498.
38. H. Hoffman, G. Salbeck, Chem. Ber. 1970, 103, 2768.
39. Opening of 3,4-epoxyflavan with phenol gives the cis-alcohol, while opening with phenoxide gives the trans-alcohol: G. Bateman, B. R. Brown, J. B. Campbell, C. A. Cotton, P. Johnson, P. Mulqueen, D. O'Neill, M. R. Shaw, R. A. Smith, J. A. Troke, J. Chem. Soc., Perkin Trans. 1 1983, 2903. In our case, however, 3,4-epoxychroman 5 gave rise to the same alcohol either with phenol or with phenoxide, with the stereochemistry tentatively assigned as trans.
40. [11a] J. E. Baldwin, J. Chem. Soc., Chem. Commun. 1976, 734.
41. [11b] J. E. Baldwin, J. Cutting, W. Dupont, L. Kruse, L. Silberman, R. C. Thomas, J. Chem. Soc., Chem. Commun. 1976, 736.
42. [11c] J. E. Baldwin, J. Chem. Soc., Chem. Commun. 1976, 738.
43. [11d] J. E. Baldwin, L. I. Kruse, J. Chem. Soc., Chem. Commun. 1977, 233.
44. Selected examples for 5-exo-trig cyclization: [12a] L. W. Manapace, H. G. Kuivila, J. Am. Chem. Soc. 1964, 86, 3047.
45. [12b] J. W. Wilt, L. L. Maravetz, J. F. Zawadski, J. Org. Chem. 1966, 31, 3018.
46. [12c] T. Sato, N. Nakamura, K. Ikeda, M. Okada, H. Ishibashi, M. Ikeda, J. Chem. Soc., Perkin Trans. 1 1992, 2399.
47. [12d] D. Crich, Q. Yao, J. Chem. Soc., Chem. Commun. 1993, 1265.
48. [12e] D. L. J. Clive, M. Cantin, J. Chem. Soc., Chem. Commun. 1995, 319, references cited therein.
49. [12f] L. Ripa, A. Hallberg, J. Org. Chem. 1998, 63, 84.
50. [12g] C. Chatgilialogulu, T. S. Gimisis, G. P. Spada, Chem. Eur. J. 1999, 5, 2866.
51. [12h] Y. Nonami, J. Baran, S. Janusz, H. Mayr, A. Masuyama, M. Nojima, J. Org. Chem. 1999, 64, 4060.
52. [12i] D. T. Davies, N. Kapur, A. F. Parsons, Tetrahedron 2000, 56, 3941.
53. [13a] R. Hug, G. Frater, H. J. Hansen, H. Schmid, Helv. Chem. Acta. 1971, 54, 306.
54. [13b] J. Hlubucek, E. Ritchie, W. C. Taylor, Aust. J. Chem. 1971, 24, 2347.
55. [14a] D. L. Hughes, Org. Prep. Proced. Int. 1996, 28, 127.
56. [14b] J. A. Dodge, S. A. Jones, Recent Res. Dev. Org. Chem. 1997, 1, 273 and references cited there in.
57. K. C. Santhosh, K. K. Balasubramanian, Synth. Commun. 1994, 1049.
58. R. Binns, W. D. Cotterill, R. Livingstone, J. Chem. Soc. C 1966, 2013.