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Volumn 61, Issue 17, 1996, Pages 5793-5800

Preparation of oxepanes, oxepenes, and oxocanes by iodoetherification using Bis(sym-collidine)iodine(I) hexafluorophosphate as electrophile

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EID: 0000742930     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960506t     Document Type: Article
Times cited : (52)

References (81)
  • 1
    • 37049105062 scopus 로고
    • For reviews on marine products see: Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251 and 551; 1986, 3, 1; 1987, 4, 539; 1988, 5, 613; 1990, 7, 269; 1991, 8, 97; 1992, 9, 323; 1993, 10, 497; 1994, 11, 355; 1995, 12, 223.
    • (1984) Nat. Prod. Rep. , vol.1 , pp. 251
    • Faulkner, D.J.1
  • 2
    • 37049105062 scopus 로고
    • For reviews on marine products see: Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251 and 551; 1986, 3, 1; 1987, 4, 539; 1988, 5, 613; 1990, 7, 269; 1991, 8, 97; 1992, 9, 323; 1993, 10, 497; 1994, 11, 355; 1995, 12, 223.
    • (1986) Nat. Prod. Rep. , vol.3 , pp. 1
  • 3
    • 0023430057 scopus 로고
    • For reviews on marine products see: Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251 and 551; 1986, 3, 1; 1987, 4, 539; 1988, 5, 613; 1990, 7, 269; 1991, 8, 97; 1992, 9, 323; 1993, 10, 497; 1994, 11, 355; 1995, 12, 223.
    • (1987) Nat. Prod. Rep. , vol.4 , pp. 539
  • 4
    • 0024205115 scopus 로고
    • For reviews on marine products see: Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251 and 551; 1986, 3, 1; 1987, 4, 539; 1988, 5, 613; 1990, 7, 269; 1991, 8, 97; 1992, 9, 323; 1993, 10, 497; 1994, 11, 355; 1995, 12, 223.
    • (1988) Nat. Prod. Rep. , vol.5 , pp. 613
  • 5
    • 0025475193 scopus 로고
    • For reviews on marine products see: Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251 and 551; 1986, 3, 1; 1987, 4, 539; 1988, 5, 613; 1990, 7, 269; 1991, 8, 97; 1992, 9, 323; 1993, 10, 497; 1994, 11, 355; 1995, 12, 223.
    • (1990) Nat. Prod. Rep. , vol.7 , pp. 269
  • 6
    • 37049105062 scopus 로고
    • For reviews on marine products see: Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251 and 551; 1986, 3, 1; 1987, 4, 539; 1988, 5, 613; 1990, 7, 269; 1991, 8, 97; 1992, 9, 323; 1993, 10, 497; 1994, 11, 355; 1995, 12, 223.
    • (1991) Nat. Prod. Rep. , vol.8 , pp. 97
  • 7
    • 0000372491 scopus 로고
    • For reviews on marine products see: Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251 and 551; 1986, 3, 1; 1987, 4, 539; 1988, 5, 613; 1990, 7, 269; 1991, 8, 97; 1992, 9, 323; 1993, 10, 497; 1994, 11, 355; 1995, 12, 223.
    • (1992) Nat. Prod. Rep. , vol.9 , pp. 323
  • 8
    • 0027672335 scopus 로고
    • For reviews on marine products see: Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251 and 551; 1986, 3, 1; 1987, 4, 539; 1988, 5, 613; 1990, 7, 269; 1991, 8, 97; 1992, 9, 323; 1993, 10, 497; 1994, 11, 355; 1995, 12, 223.
    • (1993) Nat. Prod. Rep. , vol.10 , pp. 497
  • 9
    • 0028093929 scopus 로고
    • For reviews on marine products see: Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251 and 551; 1986, 3, 1; 1987, 4, 539; 1988, 5, 613; 1990, 7, 269; 1991, 8, 97; 1992, 9, 323; 1993, 10, 497; 1994, 11, 355; 1995, 12, 223.
    • (1994) Nat. Prod. Rep. , vol.11 , pp. 355
  • 10
    • 0029107374 scopus 로고
    • For reviews on marine products see: Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251 and 551; 1986, 3, 1; 1987, 4, 539; 1988, 5, 613; 1990, 7, 269; 1991, 8, 97; 1992, 9, 323; 1993, 10, 497; 1994, 11, 355; 1995, 12, 223.
    • (1995) Nat. Prod. Rep. , vol.12 , pp. 223
  • 11
    • 37049079071 scopus 로고
    • For terrestrial products, see, for example: (a) Kawahara, N.; Nozawa, K.; Nakajima, S.; Kawai, K.-i.; Yamazaki, M. J. Chem. Soc., Chem. Commun. 1989, 951. (b) Kawahara, N.; Nozawa, K.; Yamazaki, M.; Nakajima, S.; Kawai, K. Chem. Pharm. Bull. 1990, 38, 73. (c) Kanoja, R. M.; Wachter, M. P.; Levine, S. D.; Adams, R. E.; Chen, R.; Chin, E.; Cotter, M. L.; Hirsch, A. F.; Huettemann, R.; Kane, V. V.; Ostrowski, P.; Shaw, C. J.; Mateos, J. L.; Noriega, L.; Guzman, A.; Mijarez, A.; Tovar, L.; Shefter, E. J. Org. Chem. 1982, 47, 1310. (d) Aida, M.; Shinomiya, K.; Matsuzawa, Y.; Hano, Y.; Nomura, T. Heterocycles 1994, 39, 847. (e) Cimino, G.; Madaio, A.; Trivellone, E.; Uriz, M. J. Nat. Prod. 1994, 57, 784. (f) Escher, S.; Niclass, Y. Helv. Chim. Acta 1991, 74, 179. (g) Macias, F. A.; Molinillo, J. M. G.; Varela, R. M.; Torres, A.; Fronczek, F. R. J. Org. Chem. 1994, 59, 8261.
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 951
    • Kawahara, N.1    Nozawa, K.2    Nakajima, S.3    Kawai, K.-I.4    Yamazaki, M.5
  • 12
    • 0025254529 scopus 로고
    • For terrestrial products, see, for example: (a) Kawahara, N.; Nozawa, K.; Nakajima, S.; Kawai, K.-i.; Yamazaki, M. J. Chem. Soc., Chem. Commun. 1989, 951. (b) Kawahara, N.; Nozawa, K.; Yamazaki, M.; Nakajima, S.; Kawai, K. Chem. Pharm. Bull. 1990, 38, 73. (c) Kanoja, R. M.; Wachter, M. P.; Levine, S. D.; Adams, R. E.; Chen, R.; Chin, E.; Cotter, M. L.; Hirsch, A. F.; Huettemann, R.; Kane, V. V.; Ostrowski, P.; Shaw, C. J.; Mateos, J. L.; Noriega, L.; Guzman, A.; Mijarez, A.; Tovar, L.; Shefter, E. J. Org. Chem. 1982, 47, 1310. (d) Aida, M.; Shinomiya, K.; Matsuzawa, Y.; Hano, Y.; Nomura, T. Heterocycles 1994, 39, 847. (e) Cimino, G.; Madaio, A.; Trivellone, E.; Uriz, M. J. Nat. Prod. 1994, 57, 784. (f) Escher, S.; Niclass, Y. Helv. Chim. Acta 1991, 74, 179. (g) Macias, F. A.; Molinillo, J. M. G.; Varela, R. M.; Torres, A.; Fronczek, F. R. J. Org. Chem. 1994, 59, 8261.
    • (1990) Chem. Pharm. Bull. , vol.38 , pp. 73
    • Kawahara, N.1    Nozawa, K.2    Yamazaki, M.3    Nakajima, S.4    Kawai, K.5
  • 13
    • 0019941393 scopus 로고
    • For terrestrial products, see, for example: (a) Kawahara, N.; Nozawa, K.; Nakajima, S.; Kawai, K.-i.; Yamazaki, M. J. Chem. Soc., Chem. Commun. 1989, 951. (b) Kawahara, N.; Nozawa, K.; Yamazaki, M.; Nakajima, S.; Kawai, K. Chem. Pharm. Bull. 1990, 38, 73. (c) Kanoja, R. M.; Wachter, M. P.; Levine, S. D.; Adams, R. E.; Chen, R.; Chin, E.; Cotter, M. L.; Hirsch, A. F.; Huettemann, R.; Kane, V. V.; Ostrowski, P.; Shaw, C. J.; Mateos, J. L.; Noriega, L.; Guzman, A.; Mijarez, A.; Tovar, L.; Shefter, E. J. Org. Chem. 1982, 47, 1310. (d) Aida, M.; Shinomiya, K.; Matsuzawa, Y.; Hano, Y.; Nomura, T. Heterocycles 1994, 39, 847. (e) Cimino, G.; Madaio, A.; Trivellone, E.; Uriz, M. J. Nat. Prod. 1994, 57, 784. (f) Escher, S.; Niclass, Y. Helv. Chim. Acta 1991, 74, 179. (g) Macias, F. A.; Molinillo, J. M. G.; Varela, R. M.; Torres, A.; Fronczek, F. R. J. Org. Chem. 1994, 59, 8261.
    • (1982) J. Org. Chem. , vol.47 , pp. 1310
    • Kanoja, R.M.1    Wachter, M.P.2    Levine, S.D.3    Adams, R.E.4    Chen, R.5    Chin, E.6    Cotter, M.L.7    Hirsch, A.F.8    Huettemann, R.9    Kane, V.V.10    Ostrowski, P.11    Shaw, C.J.12    Mateos, J.L.13    Noriega, L.14    Guzman, A.15    Mijarez, A.16    Tovar, L.17    Shefter, E.18
  • 14
    • 0002812677 scopus 로고
    • For terrestrial products, see, for example: (a) Kawahara, N.; Nozawa, K.; Nakajima, S.; Kawai, K.-i.; Yamazaki, M. J. Chem. Soc., Chem. Commun. 1989, 951. (b) Kawahara, N.; Nozawa, K.; Yamazaki, M.; Nakajima, S.; Kawai, K. Chem. Pharm. Bull. 1990, 38, 73. (c) Kanoja, R. M.; Wachter, M. P.; Levine, S. D.; Adams, R. E.; Chen, R.; Chin, E.; Cotter, M. L.; Hirsch, A. F.; Huettemann, R.; Kane, V. V.; Ostrowski, P.; Shaw, C. J.; Mateos, J. L.; Noriega, L.; Guzman, A.; Mijarez, A.; Tovar, L.; Shefter, E. J. Org. Chem. 1982, 47, 1310. (d) Aida, M.; Shinomiya, K.; Matsuzawa, Y.; Hano, Y.; Nomura, T. Heterocycles 1994, 39, 847. (e) Cimino, G.; Madaio, A.; Trivellone, E.; Uriz, M. J. Nat. Prod. 1994, 57, 784. (f) Escher, S.; Niclass, Y. Helv. Chim. Acta 1991, 74, 179. (g) Macias, F. A.; Molinillo, J. M. G.; Varela, R. M.; Torres, A.; Fronczek, F. R. J. Org. Chem. 1994, 59, 8261.
    • (1994) Heterocycles , vol.39 , pp. 847
    • Aida, M.1    Shinomiya, K.2    Matsuzawa, Y.3    Hano, Y.4    Nomura, T.5
  • 15
    • 0027997205 scopus 로고
    • For terrestrial products, see, for example: (a) Kawahara, N.; Nozawa, K.; Nakajima, S.; Kawai, K.-i.; Yamazaki, M. J. Chem. Soc., Chem. Commun. 1989, 951. (b) Kawahara, N.; Nozawa, K.; Yamazaki, M.; Nakajima, S.; Kawai, K. Chem. Pharm. Bull. 1990, 38, 73. (c) Kanoja, R. M.; Wachter, M. P.; Levine, S. D.; Adams, R. E.; Chen, R.; Chin, E.; Cotter, M. L.; Hirsch, A. F.; Huettemann, R.; Kane, V. V.; Ostrowski, P.; Shaw, C. J.; Mateos, J. L.; Noriega, L.; Guzman, A.; Mijarez, A.; Tovar, L.; Shefter, E. J. Org. Chem. 1982, 47, 1310. (d) Aida, M.; Shinomiya, K.; Matsuzawa, Y.; Hano, Y.; Nomura, T. Heterocycles 1994, 39, 847. (e) Cimino, G.; Madaio, A.; Trivellone, E.; Uriz, M. J. Nat. Prod. 1994, 57, 784. (f) Escher, S.; Niclass, Y. Helv. Chim. Acta 1991, 74, 179. (g) Macias, F. A.; Molinillo, J. M. G.; Varela, R. M.; Torres, A.; Fronczek, F. R. J. Org. Chem. 1994, 59, 8261.
    • (1994) J. Nat. Prod. , vol.57 , pp. 784
    • Cimino, G.1    Madaio, A.2    Trivellone, E.3    Uriz, M.4
  • 16
    • 84987453395 scopus 로고
    • For terrestrial products, see, for example: (a) Kawahara, N.; Nozawa, K.; Nakajima, S.; Kawai, K.-i.; Yamazaki, M. J. Chem. Soc., Chem. Commun. 1989, 951. (b) Kawahara, N.; Nozawa, K.; Yamazaki, M.; Nakajima, S.; Kawai, K. Chem. Pharm. Bull. 1990, 38, 73. (c) Kanoja, R. M.; Wachter, M. P.; Levine, S. D.; Adams, R. E.; Chen, R.; Chin, E.; Cotter, M. L.; Hirsch, A. F.; Huettemann, R.; Kane, V. V.; Ostrowski, P.; Shaw, C. J.; Mateos, J. L.; Noriega, L.; Guzman, A.; Mijarez, A.; Tovar, L.; Shefter, E. J. Org. Chem. 1982, 47, 1310. (d) Aida, M.; Shinomiya, K.; Matsuzawa, Y.; Hano, Y.; Nomura, T. Heterocycles 1994, 39, 847. (e) Cimino, G.; Madaio, A.; Trivellone, E.; Uriz, M. J. Nat. Prod. 1994, 57, 784. (f) Escher, S.; Niclass, Y. Helv. Chim. Acta 1991, 74, 179. (g) Macias, F. A.; Molinillo, J. M. G.; Varela, R. M.; Torres, A.; Fronczek, F. R. J. Org. Chem. 1994, 59, 8261.
    • (1991) Helv. Chim. Acta , vol.74 , pp. 179
    • Escher, S.1    Niclass, Y.2
  • 17
    • 0028593823 scopus 로고
    • For terrestrial products, see, for example: (a) Kawahara, N.; Nozawa, K.; Nakajima, S.; Kawai, K.-i.; Yamazaki, M. J. Chem. Soc., Chem. Commun. 1989, 951. (b) Kawahara, N.; Nozawa, K.; Yamazaki, M.; Nakajima, S.; Kawai, K. Chem. Pharm. Bull. 1990, 38, 73. (c) Kanoja, R. M.; Wachter, M. P.; Levine, S. D.; Adams, R. E.; Chen, R.; Chin, E.; Cotter, M. L.; Hirsch, A. F.; Huettemann, R.; Kane, V. V.; Ostrowski, P.; Shaw, C. J.; Mateos, J. L.; Noriega, L.; Guzman, A.; Mijarez, A.; Tovar, L.; Shefter, E. J. Org. Chem. 1982, 47, 1310. (d) Aida, M.; Shinomiya, K.; Matsuzawa, Y.; Hano, Y.; Nomura, T. Heterocycles 1994, 39, 847. (e) Cimino, G.; Madaio, A.; Trivellone, E.; Uriz, M. J. Nat. Prod. 1994, 57, 784. (f) Escher, S.; Niclass, Y. Helv. Chim. Acta 1991, 74, 179. (g) Macias, F. A.; Molinillo, J. M. G.; Varela, R. M.; Torres, A.; Fronczek, F. R. J. Org. Chem. 1994, 59, 8261.
    • (1994) J. Org. Chem. , vol.59 , pp. 8261
    • Macias, F.A.1    Molinillo, J.M.G.2    Varela, R.M.3    Torres, A.4    Fronczek, F.R.5
  • 18
    • 85022720403 scopus 로고
    • Atta-ur-Rahman, Ed.; Elsevier Science Publishers B.V.: New York
    • For a review see: Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science Publishers B.V.: New York, 1992; Vol. 10, pp 201-239.
    • (1992) Studies in Natural Products Chemistry , vol.10 , pp. 201-239
    • Moody, C.J.1    Davies, M.J.2
  • 19
    • 0028893499 scopus 로고
    • For a review on medium ring lactones see: Rousseau, G. Tetrahedron 1995, 43, 2777.
    • (1995) Tetrahedron , vol.43 , pp. 2777
    • Rousseau, G.1
  • 40
    • 0001329983 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: New York
    • For a review, see: Harding, K. E.; Tiner, T. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 4, p 363.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 363
    • Harding, K.E.1    Tiner, T.H.2
  • 51
    • 0000012312 scopus 로고
    • Morisson, J. D., Ed.; Academic Press: Orlando, FL
    • (b) Bartlett, P. A. In Asymmetric Synthesis; Morisson, J. D., Ed.; Academic Press: Orlando, FL, 1984; p 411.
    • (1984) Asymmetric Synthesis , pp. 411
    • Bartlett, P.A.1
  • 61
    • 4243068283 scopus 로고    scopus 로고
    • note
    • The formation of oxepanes occurred in similar yields using the more electrophilic bis(collidine)bromined) hexafluorophosphate. In this case, the cyclization could be achieved with the tetrahydropyranyl ethers. For example: 66% yield in 2-(bromomethyl)-7-(2-methylethyl)-oxepane from 2d-OTHP.
  • 68
    • 85087251016 scopus 로고    scopus 로고
    • note
    • 24 results that show that bis(pyridine)-iodine(I) hexafluorophosphate was less efficient than the corresponding collidine reagent in iodolactonizations. This seems to imply that the base is fixed on the iodonium in the intermediate.


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