A new method for the preparation of the 6,6 and 6,7 ring systems of bicyclic ethers

Tetrahedron

Volumn 54, Issue 44, 1998, Pages 13557-13566

  Simart, Fabienne ^a   Brunel, Yves ^a   Robin, Sylvie ^a   Rousseau, Gérard ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

Cyclization; Enol ethers; Halogens and compounds; Oxepanes

Indexed keywords

2,7 DIOXABICYCLO[4.4.0]DECANE DERIVATIVE; 2,8 DIOXABICYCLO[5.4.0]UNDECANE DERIVATIVE; BICYCLO COMPOUND; DECALIN DERIVATIVE; ETHER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0032578717     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00833-3     Document Type: Article

References (34)

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5. 3. For some recent results see: Oishi, T.; Nagumo, Y.; Hirama, M. J. C. S., Chem. Comm. 1998, 1041. Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917. Gleason, M.M.; McDonald, F.E. J. Org. Chem. 1997, 62, 6432. Clark, J.S.; Kettle, J.G. Tetrahedron Lett. 1997, 38, 127. Atsuta, H.; Fujiwara, K.; Murai, A. Synlett. 1997, 307. Alvarez, E.; Pérez, R.; Rico, M.; Rodriguez, M. R.; Martin, J. D. J. Org. Chem. 1996, 61, 3003.
6. 3. For some recent results see: Oishi, T.; Nagumo, Y.; Hirama, M. J. C. S., Chem. Comm. 1998, 1041. Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917. Gleason, M.M.; McDonald, F.E. J. Org. Chem. 1997, 62, 6432. Clark, J.S.; Kettle, J.G. Tetrahedron Lett. 1997, 38, 127. Atsuta, H.; Fujiwara, K.; Murai, A. Synlett. 1997, 307. Alvarez, E.; Pérez, R.; Rico, M.; Rodriguez, M. R.; Martin, J. D. J. Org. Chem. 1996, 61, 3003.
7. 3. For some recent results see: Oishi, T.; Nagumo, Y.; Hirama, M. J. C. S., Chem. Comm. 1998, 1041. Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917. Gleason, M.M.; McDonald, F.E. J. Org. Chem. 1997, 62, 6432. Clark, J.S.; Kettle, J.G. Tetrahedron Lett. 1997, 38, 127. Atsuta, H.; Fujiwara, K.; Murai, A. Synlett. 1997, 307. Alvarez, E.; Pérez, R.; Rico, M.; Rodriguez, M. R.; Martin, J. D. J. Org. Chem. 1996, 61, 3003.
8. 3. For some recent results see: Oishi, T.; Nagumo, Y.; Hirama, M. J. C. S., Chem. Comm. 1998, 1041. Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917. Gleason, M.M.; McDonald, F.E. J. Org. Chem. 1997, 62, 6432. Clark, J.S.; Kettle, J.G. Tetrahedron Lett. 1997, 38, 127. Atsuta, H.; Fujiwara, K.; Murai, A. Synlett. 1997, 307. Alvarez, E.; Pérez, R.; Rico, M.; Rodriguez, M. R.; Martin, J. D. J. Org. Chem. 1996, 61, 3003.
9. 3. For some recent results see: Oishi, T.; Nagumo, Y.; Hirama, M. J. C. S., Chem. Comm. 1998, 1041. Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917. Gleason, M.M.; McDonald, F.E. J. Org. Chem. 1997, 62, 6432. Clark, J.S.; Kettle, J.G. Tetrahedron Lett. 1997, 38, 127. Atsuta, H.; Fujiwara, K.; Murai, A. Synlett. 1997, 307. Alvarez, E.; Pérez, R.; Rico, M.; Rodriguez, M. R.; Martin, J. D. J. Org. Chem. 1996, 61, 3003.
10. 4. Hemibrevetoxin B: Nicolaou, K.C.; Reddy, K.R.; Skokotos, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.K. J. Am. Chem. Soc. 1993, 115, 3558. Kadota, I.; Park, J.Y.; Koumura, N.; Polland, G.; Matsokawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777. Ishihara, J.; Murai, A. Synlett 1996, 363. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365. Mori, Y.; Yaegashi, K. Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Brevetoxin B: Nicolaou, K.C.; Theodorakis, E.E.; Rutjes, F.P.J.T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao, X.-Y. J. Am. Chem. Soc. 1995, 117, 1171. Nicolaou, K.C; Rutjes, F.P.J.T.; Theodorakis, E.A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173. See: Nicolaou, K.C. Angew. Chem. Int. Ed. Engl. 1996, 35, 589.
11. 4. Hemibrevetoxin B: Nicolaou, K.C.; Reddy, K.R.; Skokotos, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.K. J. Am. Chem. Soc. 1993, 115, 3558. Kadota, I.; Park, J.Y.; Koumura, N.; Polland, G.; Matsokawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777. Ishihara, J.; Murai, A. Synlett 1996, 363. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365. Mori, Y.; Yaegashi, K. Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Brevetoxin B: Nicolaou, K.C.; Theodorakis, E.E.; Rutjes, F.P.J.T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao, X.-Y. J. Am. Chem. Soc. 1995, 117, 1171. Nicolaou, K.C; Rutjes, F.P.J.T.; Theodorakis, E.A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173. See: Nicolaou, K.C. Angew. Chem. Int. Ed. Engl. 1996, 35, 589.
12. 4. Hemibrevetoxin B: Nicolaou, K.C.; Reddy, K.R.; Skokotos, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.K. J. Am. Chem. Soc. 1993, 115, 3558. Kadota, I.; Park, J.Y.; Koumura, N.; Polland, G.; Matsokawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777. Ishihara, J.; Murai, A. Synlett 1996, 363. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365. Mori, Y.; Yaegashi, K. Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Brevetoxin B: Nicolaou, K.C.; Theodorakis, E.E.; Rutjes, F.P.J.T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao, X.-Y. J. Am. Chem. Soc. 1995, 117, 1171. Nicolaou, K.C; Rutjes, F.P.J.T.; Theodorakis, E.A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173. See: Nicolaou, K.C. Angew. Chem. Int. Ed. Engl. 1996, 35, 589.
13. 4. Hemibrevetoxin B: Nicolaou, K.C.; Reddy, K.R.; Skokotos, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.K. J. Am. Chem. Soc. 1993, 115, 3558. Kadota, I.; Park, J.Y.; Koumura, N.; Polland, G.; Matsokawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777. Ishihara, J.; Murai, A. Synlett 1996, 363. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365. Mori, Y.; Yaegashi, K. Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Brevetoxin B: Nicolaou, K.C.; Theodorakis, E.E.; Rutjes, F.P.J.T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao, X.-Y. J. Am. Chem. Soc. 1995, 117, 1171. Nicolaou, K.C; Rutjes, F.P.J.T.; Theodorakis, E.A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173. See: Nicolaou, K.C. Angew. Chem. Int. Ed. Engl. 1996, 35, 589.
14. 4. Hemibrevetoxin B: Nicolaou, K.C.; Reddy, K.R.; Skokotos, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.K. J. Am. Chem. Soc. 1993, 115, 3558. Kadota, I.; Park, J.Y.; Koumura, N.; Polland, G.; Matsokawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777. Ishihara, J.; Murai, A. Synlett 1996, 363. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365. Mori, Y.; Yaegashi, K. Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Brevetoxin B: Nicolaou, K.C.; Theodorakis, E.E.; Rutjes, F.P.J.T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao, X.-Y. J. Am. Chem. Soc. 1995, 117, 1171. Nicolaou, K.C; Rutjes, F.P.J.T.; Theodorakis, E.A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173. See: Nicolaou, K.C. Angew. Chem. Int. Ed. Engl. 1996, 35, 589.
15. 4. Hemibrevetoxin B: Nicolaou, K.C.; Reddy, K.R.; Skokotos, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.K. J. Am. Chem. Soc. 1993, 115, 3558. Kadota, I.; Park, J.Y.; Koumura, N.; Polland, G.; Matsokawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777. Ishihara, J.; Murai, A. Synlett 1996, 363. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365. Mori, Y.; Yaegashi, K. Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Brevetoxin B: Nicolaou, K.C.; Theodorakis, E.E.; Rutjes, F.P.J.T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao, X.-Y. J. Am. Chem. Soc. 1995, 117, 1171. Nicolaou, K.C; Rutjes, F.P.J.T.; Theodorakis, E.A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173. See: Nicolaou, K.C. Angew. Chem. Int. Ed. Engl. 1996, 35, 589.
16. 4. Hemibrevetoxin B: Nicolaou, K.C.; Reddy, K.R.; Skokotos, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.K. J. Am. Chem. Soc. 1993, 115, 3558. Kadota, I.; Park, J.Y.; Koumura, N.; Polland, G.; Matsokawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777. Ishihara, J.; Murai, A. Synlett 1996, 363. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365. Mori, Y.; Yaegashi, K. Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Brevetoxin B: Nicolaou, K.C.; Theodorakis, E.E.; Rutjes, F.P.J.T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao, X.-Y. J. Am. Chem. Soc. 1995, 117, 1171. Nicolaou, K.C; Rutjes, F.P.J.T.; Theodorakis, E.A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173. See: Nicolaou, K.C. Angew. Chem. Int. Ed. Engl. 1996, 35, 589.
17. 4. Hemibrevetoxin B: Nicolaou, K.C.; Reddy, K.R.; Skokotos, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.K. J. Am. Chem. Soc. 1993, 115, 3558. Kadota, I.; Park, J.Y.; Koumura, N.; Polland, G.; Matsokawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777. Ishihara, J.; Murai, A. Synlett 1996, 363. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365. Mori, Y.; Yaegashi, K. Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Brevetoxin B: Nicolaou, K.C.; Theodorakis, E.E.; Rutjes, F.P.J.T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao, X.-Y. J. Am. Chem. Soc. 1995, 117, 1171. Nicolaou, K.C; Rutjes, F.P.J.T.; Theodorakis, E.A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173. See: Nicolaou, K.C. Angew. Chem. Int. Ed. Engl. 1996, 35, 589.
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22. 5. Suzuki, K.; Mukaiyama, T. Chem. Lett. 1982, 683 and 1525. Ting, P. C.; Bartlett, P. A. J. Am. Chem. Soc. 1984,106, 2668. Paquet, F.; Sinaÿ, P. Tetrahedron Lett. 1984, 25, 3071. Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. Doyle, M. P.; Griffin, J.H., Chinn, M. S.; Van Leusen, D. J. Org. Chem. 1984, 49, 1917. Ha, D.-C.; Hart, D. J. Tetrahedron Lett. 1987, 28, 4489. Kerwin, S.M.; Paul, A.G.; Heathcock, C.H. J. Org. Chem. 1987, 52, 1686. Koft, E. R.; Dorff, P.; Kullnig, R. J. Org. Chem. 1989, 54, 2936. Fabre, V.; Lila, C.; Saroli, A.; Doutheau, A. Tetrahedron 1989, 45, 7765. Vlahov, I. R.; Vlahova, P. I.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 7503. Maudrin, J.; Barrère, B.; Chantegrel, B.; Deshayes, C.; Quash, G.; Doutheau, A. Bull. Soc. Chim. Fr. 1994, 131, 400. Devasagayaraj, A.; Schwink, L.; Knochel, P. J. Org. Chem. 1995, 60, 3311.
23. 5. Suzuki, K.; Mukaiyama, T. Chem. Lett. 1982, 683 and 1525. Ting, P. C.; Bartlett, P. A. J. Am. Chem. Soc. 1984,106, 2668. Paquet, F.; Sinaÿ, P. Tetrahedron Lett. 1984, 25, 3071. Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. Doyle, M. P.; Griffin, J.H., Chinn, M. S.; Van Leusen, D. J. Org. Chem. 1984, 49, 1917. Ha, D.-C.; Hart, D. J. Tetrahedron Lett. 1987, 28, 4489. Kerwin, S.M.; Paul, A.G.; Heathcock, C.H. J. Org. Chem. 1987, 52, 1686. Koft, E. R.; Dorff, P.; Kullnig, R. J. Org. Chem. 1989, 54, 2936. Fabre, V.; Lila, C.; Saroli, A.; Doutheau, A. Tetrahedron 1989, 45, 7765. Vlahov, I. R.; Vlahova, P. I.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 7503. Maudrin, J.; Barrère, B.; Chantegrel, B.; Deshayes, C.; Quash, G.; Doutheau, A. Bull. Soc. Chim. Fr. 1994, 131, 400. Devasagayaraj, A.; Schwink, L.; Knochel, P. J. Org. Chem. 1995, 60, 3311.
24. 5. Suzuki, K.; Mukaiyama, T. Chem. Lett. 1982, 683 and 1525. Ting, P. C.; Bartlett, P. A. J. Am. Chem. Soc. 1984,106, 2668. Paquet, F.; Sinaÿ, P. Tetrahedron Lett. 1984, 25, 3071. Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. Doyle, M. P.; Griffin, J.H., Chinn, M. S.; Van Leusen, D. J. Org. Chem. 1984, 49, 1917. Ha, D.-C.; Hart, D. J. Tetrahedron Lett. 1987, 28, 4489. Kerwin, S.M.; Paul, A.G.; Heathcock, C.H. J. Org. Chem. 1987, 52, 1686. Koft, E. R.; Dorff, P.; Kullnig, R. J. Org. Chem. 1989, 54, 2936. Fabre, V.; Lila, C.; Saroli, A.; Doutheau, A. Tetrahedron 1989, 45, 7765. Vlahov, I. R.; Vlahova, P. I.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 7503. Maudrin, J.; Barrère, B.; Chantegrel, B.; Deshayes, C.; Quash, G.; Doutheau, A. Bull. Soc. Chim. Fr. 1994, 131, 400. Devasagayaraj, A.; Schwink, L.; Knochel, P. J. Org. Chem. 1995, 60, 3311.
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