A conjugate addition-radical cyclisation approach to sesquiterpene-phenol natural products

Journal of the Chemical Society. Perkin Transactions 1

Volumn , Issue 2, 2001, Pages 206-215

  Crombie, Barry S ^a   Smith, Colin ^a   Varnavas, Christalla Z ^a   Wallace, Timothy W ^a  

^a UNIVERSITY OF SALFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALKYLATION; CATALYSTS; ESTERS; MANGANESE COMPOUNDS; OXIDATION;

RADICAL CYCLIZATION;

PHENOLS;

EID: 0035925006     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/b005617k     Document Type: Article

References (56)

1. For a review, see D.J. Faulkner, Nat. Prod. Rep., 1996, 13, 75.
2. B.N. Ravi, H.P. Perzanowski, R.A. Ross, T.R. Erdman, P.J. Scheuer, J. Finer and J. Clardy, Pure Appl. Chem., 1979, 51, 1893; M.T. Hamann, P.J. Scheuer and M. Kelly-Borges, J. Org. Chem., 1993, 58, 6565.
3. B.N. Ravi, H.P. Perzanowski, R.A. Ross, T.R. Erdman, P.J. Scheuer, J. Finer and J. Clardy, Pure Appl. Chem., 1979, 51, 1893; M.T. Hamann, P.J. Scheuer and M. Kelly-Borges, J. Org. Chem., 1993, 58, 6565.
4. M.T. Hamann and P.J. Scheuer, Tetrahedron Lett., 1991, 32, 5671.
5. S.S. Nasu, B.K.S. Yeung, M.T. Hamann, P.J. Scheuer, M. Kelly-Borges and K. Goins, J. Org. Chem., 1995, 60, 7290.
6. M.-L. Bourguet-Kondracki, C. Debitus and M. Guyot, Tetrahedron Lett., 1996, 37, 3861 and references cited therein.
7. P. Djura, D.B. Stierle, B. Sullivan, D.J. Faulkner, E. Arnold and J. Clardy, J. Org. Chem., 1980, 45, 1435; J. Rodriguez, E. Quiñoa, R. Riguera, B.M. Peters, L.M. Abrell and P. Crews, Tetrahedron, 1992, 48, 6667.
8. P. Djura, D.B. Stierle, B. Sullivan, D.J. Faulkner, E. Arnold and J. Clardy, J. Org. Chem., 1980, 45, 1435; J. Rodriguez, E. Quiñoa, R. Riguera, B.M. Peters, L.M. Abrell and P. Crews, Tetrahedron, 1992, 48, 6667.
9. R. Talpir, A. Rudi, Y. Kashman, Y. Loya and A. Hizi Tetrahedron, 1994, 50, 4179; S. Poigny, T. Huor, M. Guyot and M. Samadi, J. Org. Chem., 1999, 64, 9318.
10. R. Talpir, A. Rudi, Y. Kashman, Y. Loya and A. Hizi Tetrahedron, 1994, 50, 4179; S. Poigny, T. Huor, M. Guyot and M. Samadi, J. Org. Chem., 1999, 64, 9318.
11. K. Hirai, K.T. Suzuki and S. Nozoe, Tetrahedron, 1971, 27, 6057 and references cited therein.
12. K.A. El Sayed, P. Bartyzel, X. Shen, T.L. Perry, J.K. Zjawiony and M.T. Hamann, Tetrahedron, 2000, 56, 949.
13. For information about the status of these diseases and associated countermeasures, see the World Health Organisation's documentation at 〈http://www.who.int/inf-fs/en/fact104.html〉 and 〈http://www.who.int/health-topics/malaria.htm〉.
14. M. Kato, Y. Matsumura, K. Heima, N. Fukamiya, C. Kabuto and A. Yoshikoshi, Tetrahedron, 1987, 43, 711 and references cited therein; B.M. Trost, F.J. Fleitz and W.J. Watkins, J. Am. Chem. Soc., 1996, 118, 5146.
15. M. Kato, Y. Matsumura, K. Heima, N. Fukamiya, C. Kabuto and A. Yoshikoshi, Tetrahedron, 1987, 43, 711 and references cited therein; B.M. Trost, F.J. Fleitz and W.J. Watkins, J. Am. Chem. Soc., 1996, 118, 5146.
16. G.L. Trammell, Tetrahedron Lett., 1978, 1525; A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron Lett., 1997, 38, 2325.
17. G.L. Trammell, Tetrahedron Lett., 1978, 1525; A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron Lett., 1997, 38, 2325.
18. O. Arjona, M. Garranzo, J. Mahugo, E. Maroto, J. Plumet and B. Sáez, Tetrahedron Lett., 1997, 38, 7249.
19. K. Ishihara, S. Nakamura and H. Yamamoto, J. Am. Chem. Soc., 1999, 121, 4906.
20. S.T. Saengchantara and T.W. Wallace, Tetrahedron, 1990, 46, 3029.
21. B.B. Snider, Chem. Rev., 1996, 96, 339 and references cited therein.
22. Preliminary account and X-ray data: B.S. Crombie, A.D. Redhouse, C. Smith and T.W. Wallace, J. Chem. Soc., Chem. Commun., 1995, 403.
23. J.D. White, R.W. Skeean and G.L. Trammell, J. Org. Chem., 1985, 50, 1939.
24. G.M. Coppola and R.W. Dodsworth, Synthesis, 1981, 523.
25. D. Herlem, J. Kervagoret, D. Yu, F. Khuong-Huu and A.S. Kende, Tetrahedron, 1993, 49, 607. Dihydro-β-ionone 20 is also available commercially (Aldrich Flavors & Fragrances, W36260-3).
26. S.P. Chavan, P.K. Zubaidha, S.W. Dantale, A. Keshavaraja, A.V. Ramaswamy and T. Ravindranathan, Tetrahedron Lett., 1996, 37, 233.
27. For other examples of this process, see I. Fleming, A.K. Sarkar, M.J. Doyle and P.R. Raithby, J. Chem. Soc., Perkin Trans. 1, 1989, 2023.
28. For a review on copper-catalysed additions of organometallics, see E. Erick, Tetrahedron, 1984, 40, 641.
29. For discussions on the use of silylating agents in conjugate addition protocols, see B.H. Lipshutz, E.L. Ellsworth, T.J. Siahaan and A. Shirazi, Tetrahedron Lett., 1988, 29, 6677; S. Matsuzawa, Y. Horiguchi, E. Nakamura and I. Kuwajima, Tetrahedron, 1989, 45, 349.
30. For discussions on the use of silylating agents in conjugate addition protocols, see B.H. Lipshutz, E.L. Ellsworth, T.J. Siahaan and A. Shirazi, Tetrahedron Lett., 1988, 29, 6677; S. Matsuzawa, Y. Horiguchi, E. Nakamura and I. Kuwajima, Tetrahedron, 1989, 45, 349.
31. T. Kawanobe, K. Kogami, K. Hayashi and M. Matsui, Agric. Biol. Chem., 1984, 48, 461.
32. T. Eicher, K. Massonne and M. Herrmann, Synthesis, 1991, 1173.
33. For an alternative approach to 24, see R.C. Almanza and A.H. Reyes, Synth. Commun., 1993, 23, 867.
34. M.J. Kurth and C.J. Soares, Tetraheclron Lett., 1987, 28, 1031. See also A. Yajima, H. Takikawa and K. Mori, Liebigs Ann. Chem., 1996, 891.
35. M.J. Kurth and C.J. Soares, Tetraheclron Lett., 1987, 28, 1031. See also A. Yajima, H. Takikawa and K. Mori, Liebigs Ann. Chem., 1996, 891.
36. For a description and discussion of the methodology used to prepare 27, see D.S. Dodd and A.C. Oehlschlager, J. Org. Chem., 1992, 57, 2794 and references cited therein.
37. For related reactions and mechanistic discussions, see S.A. Kates, M.A. Dombroski and B.B. Snider, J. Org. Chem., 1990, 55, 2427; D.P. Curran, T.M. Morgan, C.E. Schwartz, B.B. Snider and M.A. Dombroski, J. Am. Chem. Soc., 1991, 113, 6607; M.I. Colombo, S. Signorella, M.P. Mischne, M. Gonzalez-Sierra and E.A. Ruveda, Tetrahedron, 1990, 46, 4149. For a pertinent review, see G.G. Melikyan, Synthesis, 1993, 833.
38. For related reactions and mechanistic discussions, see S.A. Kates, M.A. Dombroski and B.B. Snider, J. Org. Chem., 1990, 55, 2427; D.P. Curran, T.M. Morgan, C.E. Schwartz, B.B. Snider and M.A. Dombroski, J. Am. Chem. Soc., 1991, 113, 6607; M.I. Colombo, S. Signorella, M.P. Mischne, M. Gonzalez-Sierra and E.A. Ruveda, Tetrahedron, 1990, 46, 4149. For a pertinent review, see G.G. Melikyan, Synthesis, 1993, 833.
39. For related reactions and mechanistic discussions, see S.A. Kates, M.A. Dombroski and B.B. Snider, J. Org. Chem., 1990, 55, 2427; D.P. Curran, T.M. Morgan, C.E. Schwartz, B.B. Snider and M.A. Dombroski, J. Am. Chem. Soc., 1991, 113, 6607; M.I. Colombo, S. Signorella, M.P. Mischne, M. Gonzalez-Sierra and E.A. Ruveda, Tetrahedron, 1990, 46, 4149. For a pertinent review, see G.G. Melikyan, Synthesis, 1993, 833.
40. For related reactions and mechanistic discussions, see S.A. Kates, M.A. Dombroski and B.B. Snider, J. Org. Chem., 1990, 55, 2427; D.P. Curran, T.M. Morgan, C.E. Schwartz, B.B. Snider and M.A. Dombroski, J. Am. Chem. Soc., 1991, 113, 6607; M.I. Colombo, S. Signorella, M.P. Mischne, M. Gonzalez-Sierra and E.A. Ruveda, Tetrahedron, 1990, 46, 4149. For a pertinent review, see G.G. Melikyan, Synthesis, 1993, 833.
41. E.I. Heiba, R.M. Dessau and W.J. Koechl, J. Am. Chem. Soc., 1969, 91, 138.
42. Lactone formation in this type of reaction is well precedented. For examples and discussions, see B.B. Snider, J.E. Merritt, M.A. Dombroski and B.O. Buckman, J. Org. Chem., 1991, 56, 5544; B.B. Snider and B.A. McCarthy, J. Org. Chem., 1993, 58, 6217. See also E. Baciocchi, A.B. Paolobelli and R. Ruzziconi, Tetrahedron, 1992, 48, 4617; E. Baciocchi, B. Giese, H. Farshchi and R. Ruzziconi, J. Org. Chem., 1990, 55, 5688.
43. Lactone formation in this type of reaction is well precedented. For examples and discussions, see B.B. Snider, J.E. Merritt, M.A. Dombroski and B.O. Buckman, J. Org. Chem., 1991, 56, 5544; B.B. Snider and B.A. McCarthy, J. Org. Chem., 1993, 58, 6217. See also E. Baciocchi, A.B. Paolobelli and R. Ruzziconi, Tetrahedron, 1992, 48, 4617; E. Baciocchi, B. Giese, H. Farshchi and R. Ruzziconi, J. Org. Chem., 1990, 55, 5688.
44. Lactone formation in this type of reaction is well precedented. For examples and discussions, see B.B. Snider, J.E. Merritt, M.A. Dombroski and B.O. Buckman, J. Org. Chem., 1991, 56, 5544; B.B. Snider and B.A. McCarthy, J. Org. Chem., 1993, 58, 6217. See also E. Baciocchi, A.B. Paolobelli and R. Ruzziconi, Tetrahedron, 1992, 48, 4617; E. Baciocchi, B. Giese, H. Farshchi and R. Ruzziconi, J. Org. Chem., 1990, 55, 5688.
45. Lactone formation in this type of reaction is well precedented. For examples and discussions, see B.B. Snider, J.E. Merritt, M.A. Dombroski and B.O. Buckman, J. Org. Chem., 1991, 56, 5544; B.B. Snider and B.A. McCarthy, J. Org. Chem., 1993, 58, 6217. See also E. Baciocchi, A.B. Paolobelli and R. Ruzziconi, Tetrahedron, 1992, 48, 4617; E. Baciocchi, B. Giese, H. Farshchi and R. Ruzziconi, J. Org. Chem., 1990, 55, 5688.
46. P. Breuilles and D. Uguen, Bull. Soc. Chim. Fr., 1988, 705 and references cited therein.
47. For related cyclisations, see A.K. Ghosh, K. Ghosh, S. Pal and U.R. Chatak, J. Chem. Soc., Chem. Commun., 1993, 809, 1176.
48. K. Hirai, K.T. Suzuki and S. Nozoe, Tetrahedron, 1971, 27, 6057. See also S. Oida, Y. Ohashi, A. Yoshida and E. Ohki, Chem. Pharm. Bull., 1972, 20, 2634.
49. K. Hirai, K.T. Suzuki and S. Nozoe, Tetrahedron, 1971, 27, 6057. See also S. Oida, Y. Ohashi, A. Yoshida and E. Ohki, Chem. Pharm. Bull., 1972, 20, 2634.
50. D.D. Perrin, W.L.F. Armarego and D.R. Perrin, Purification of Laboratory Chemicals, 2nd edn., Pergamon, Oxford, 1980.
51. M. Casey, J. Leonard, B. Lygo and G. Procter, Advanced Practical Organic Chemistry, Blackie, Glasgow, 1990, p. 114.
52. W.C. Still, M. Khan and A. Mitra, J. Org. Chem., 1978, 43, 2923.
53. N. Müller and W. Hoffmann, Synthesis, 1975, 781.
54. G. Büchi and J.D. White, J. Am. Chem. Soc., 1964, 86, 2884. See also A. Srikrishna and K. Krishnan, J. Chem. Soc., Perkin Trans. 1, 1993, 667.
55. G. Büchi and J.D. White, J. Am. Chem. Soc., 1964, 86, 2884. See also A. Srikrishna and K. Krishnan, J. Chem. Soc., Perkin Trans. 1, 1993, 667.
56. A.G. Andrewes, G. Borch and S. Liaaen-Jensen, Acta Chem. Scand., Ser. B, 1984, 38, 871.