Stereospecific synthesis of eight- and nine-membered cyclic ethers by Eu(fod)3-mediated cyclization of hydroxy epoxides

Tetrahedron Letters

Volumn 44, Issue 13, 2003, Pages 2709-2712

  Saitoh, Toshikazu ^a   Suzuki, Toshio ^a   Onodera, Norihiro ^a   Sekiguchi, Hideya ^a   Hagiwara, Hisahiro ^a   Hoshi, Takashi ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

Cyclization; Hydroxy epoxides; Oxocenes; Oxonenes; Regioselection

Indexed keywords

EPOXIDE; ETHER DERIVATIVE; EUROPIUM DERIVATIVE; HYDROXYL GROUP; METAL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037463721     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00335-6     Document Type: Article

References (37)

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2. For reviews, see: (a) Moore, R. E. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1978; Vol. 1, pp. 43-121; (b) Erickson, K. L. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1983; Vol. 5, pp. 131-257; (c) Faulkner, D. J. Nat. Prod. Rep. 2001, 18, 1-49. See also his previous reviews in Nat. Prod. Rep.
3. For reviews, see: (a) Moore, R. E. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1978; Vol. 1, pp. 43-121; (b) Erickson, K. L. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1983; Vol. 5, pp. 131-257; (c) Faulkner, D. J. Nat. Prod. Rep. 2001, 18, 1-49. See also his previous reviews in Nat. Prod. Rep.
4. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
5. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
6. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
7. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
8. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
9. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
10. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
11. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
12. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
13. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
14. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
15. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
16. For reviews on the synthesis of medium-sized cyclic ethers, see: (a) Albizati, K.; Martin, V. A.; Agharahimi, M. R.; Stolze, D. A. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 6, pp. 69-84; (b) Elliott, M. C. Contemp. Org. Synth. 1994, 457-474. For more recent syntheses of eight-membered and nine-membered cyclic ethers, see: (c) Sakamoto, Y.; Tamegai, K.; Nakata, T. Org. Lett. 2002, 4, 675-678; (d) Matsuo, G.; Kadohara, H.; Nakata, T. Chem. Lett. 2002, 148-149; (e) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268; (f) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738; (g) Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 633-635; (h) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393-396; (i) Krüger, J.; Hoffmann R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504; (j) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614; (k) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549; (l) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300; (m) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165-1167.
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20. For examples of the use of these lanthanide complexes as Lewis acids, see: (a) Arroyo, Y.; de Paz, M.; Rodríguez, J. F.; Sanz-Tejedor, M. A.; Ruano, J. L. G. J. Org. Chem. 2002, 67, 5638-5643; (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816; (c) Tamura, O.; Mita, N.; Gotanda, K.; Yamada, K.; Nakano, T.; Katagiri, R.; Sakamoto, M. Heterocycles 1997, 46, 95-99; (d) Shull, B. K.; Sakai, T.; Koreeda, M. J. Am. Chem. Soc. 1996, 118, 11690-11691; (e) Miles, W. H.; Berreth, C. L.; Anderton, C. A. Tetrahedron Lett. 1996, 37, 7893-7896; (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987-988; (g) Gandhi, R. P.; Ishar, M. P. S.; Wali, A. J. Chem. Soc., Chem. Commun. 1988, 1074-1075; (h) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716-3717.
21. For examples of the use of these lanthanide complexes as Lewis acids, see: (a) Arroyo, Y.; de Paz, M.; Rodríguez, J. F.; Sanz-Tejedor, M. A.; Ruano, J. L. G. J. Org. Chem. 2002, 67, 5638-5643; (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816; (c) Tamura, O.; Mita, N.; Gotanda, K.; Yamada, K.; Nakano, T.; Katagiri, R.; Sakamoto, M. Heterocycles 1997, 46, 95-99; (d) Shull, B. K.; Sakai, T.; Koreeda, M. J. Am. Chem. Soc. 1996, 118, 11690-11691; (e) Miles, W. H.; Berreth, C. L.; Anderton, C. A. Tetrahedron Lett. 1996, 37, 7893-7896; (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987-988; (g) Gandhi, R. P.; Ishar, M. P. S.; Wali, A. J. Chem. Soc., Chem. Commun. 1988, 1074-1075; (h) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716-3717.
22. For examples of the use of these lanthanide complexes as Lewis acids, see: (a) Arroyo, Y.; de Paz, M.; Rodríguez, J. F.; Sanz-Tejedor, M. A.; Ruano, J. L. G. J. Org. Chem. 2002, 67, 5638-5643; (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816; (c) Tamura, O.; Mita, N.; Gotanda, K.; Yamada, K.; Nakano, T.; Katagiri, R.; Sakamoto, M. Heterocycles 1997, 46, 95-99; (d) Shull, B. K.; Sakai, T.; Koreeda, M. J. Am. Chem. Soc. 1996, 118, 11690-11691; (e) Miles, W. H.; Berreth, C. L.; Anderton, C. A. Tetrahedron Lett. 1996, 37, 7893-7896; (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987-988; (g) Gandhi, R. P.; Ishar, M. P. S.; Wali, A. J. Chem. Soc., Chem. Commun. 1988, 1074-1075; (h) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716-3717.
23. For examples of the use of these lanthanide complexes as Lewis acids, see: (a) Arroyo, Y.; de Paz, M.; Rodríguez, J. F.; Sanz-Tejedor, M. A.; Ruano, J. L. G. J. Org. Chem. 2002, 67, 5638-5643; (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816; (c) Tamura, O.; Mita, N.; Gotanda, K.; Yamada, K.; Nakano, T.; Katagiri, R.; Sakamoto, M. Heterocycles 1997, 46, 95-99; (d) Shull, B. K.; Sakai, T.; Koreeda, M. J. Am. Chem. Soc. 1996, 118, 11690-11691; (e) Miles, W. H.; Berreth, C. L.; Anderton, C. A. Tetrahedron Lett. 1996, 37, 7893-7896; (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987-988; (g) Gandhi, R. P.; Ishar, M. P. S.; Wali, A. J. Chem. Soc., Chem. Commun. 1988, 1074-1075; (h) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716-3717.
24. For examples of the use of these lanthanide complexes as Lewis acids, see: (a) Arroyo, Y.; de Paz, M.; Rodríguez, J. F.; Sanz-Tejedor, M. A.; Ruano, J. L. G. J. Org. Chem. 2002, 67, 5638-5643; (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816; (c) Tamura, O.; Mita, N.; Gotanda, K.; Yamada, K.; Nakano, T.; Katagiri, R.; Sakamoto, M. Heterocycles 1997, 46, 95-99; (d) Shull, B. K.; Sakai, T.; Koreeda, M. J. Am. Chem. Soc. 1996, 118, 11690-11691; (e) Miles, W. H.; Berreth, C. L.; Anderton, C. A. Tetrahedron Lett. 1996, 37, 7893-7896; (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987-988; (g) Gandhi, R. P.; Ishar, M. P. S.; Wali, A. J. Chem. Soc., Chem. Commun. 1988, 1074-1075; (h) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716-3717.
25. For examples of the use of these lanthanide complexes as Lewis acids, see: (a) Arroyo, Y.; de Paz, M.; Rodríguez, J. F.; Sanz-Tejedor, M. A.; Ruano, J. L. G. J. Org. Chem. 2002, 67, 5638-5643; (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816; (c) Tamura, O.; Mita, N.; Gotanda, K.; Yamada, K.; Nakano, T.; Katagiri, R.; Sakamoto, M. Heterocycles 1997, 46, 95-99; (d) Shull, B. K.; Sakai, T.; Koreeda, M. J. Am. Chem. Soc. 1996, 118, 11690-11691; (e) Miles, W. H.; Berreth, C. L.; Anderton, C. A. Tetrahedron Lett. 1996, 37, 7893-7896; (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987-988; (g) Gandhi, R. P.; Ishar, M. P. S.; Wali, A. J. Chem. Soc., Chem. Commun. 1988, 1074-1075; (h) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716-3717.
26. For examples of the use of these lanthanide complexes as Lewis acids, see: (a) Arroyo, Y.; de Paz, M.; Rodríguez, J. F.; Sanz-Tejedor, M. A.; Ruano, J. L. G. J. Org. Chem. 2002, 67, 5638-5643; (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816; (c) Tamura, O.; Mita, N.; Gotanda, K.; Yamada, K.; Nakano, T.; Katagiri, R.; Sakamoto, M. Heterocycles 1997, 46, 95-99; (d) Shull, B. K.; Sakai, T.; Koreeda, M. J. Am. Chem. Soc. 1996, 118, 11690-11691; (e) Miles, W. H.; Berreth, C. L.; Anderton, C. A. Tetrahedron Lett. 1996, 37, 7893-7896; (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987-988; (g) Gandhi, R. P.; Ishar, M. P. S.; Wali, A. J. Chem. Soc., Chem. Commun. 1988, 1074-1075; (h) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716-3717.
27. For examples of the use of these lanthanide complexes as Lewis acids, see: (a) Arroyo, Y.; de Paz, M.; Rodríguez, J. F.; Sanz-Tejedor, M. A.; Ruano, J. L. G. J. Org. Chem. 2002, 67, 5638-5643; (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816; (c) Tamura, O.; Mita, N.; Gotanda, K.; Yamada, K.; Nakano, T.; Katagiri, R.; Sakamoto, M. Heterocycles 1997, 46, 95-99; (d) Shull, B. K.; Sakai, T.; Koreeda, M. J. Am. Chem. Soc. 1996, 118, 11690-11691; (e) Miles, W. H.; Berreth, C. L.; Anderton, C. A. Tetrahedron Lett. 1996, 37, 7893-7896; (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987-988; (g) Gandhi, R. P.; Ishar, M. P. S.; Wali, A. J. Chem. Soc., Chem. Commun. 1988, 1074-1075; (h) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716-3717.
28. 3 to the formation of the seven-membered cyclic ether has been reported, see: (a) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron 1998, 54, 21-44; (b) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron Lett. 1997, 38, 8053-8056.
29. 3 to the formation of the seven-membered cyclic ether has been reported, see: (a) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron 1998, 54, 21-44; (b) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron Lett. 1997, 38, 8053-8056.
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