메뉴 건너뛰기




Volumn 5, Issue 13, 2003, Pages 2339-2342

Sime3-based homologation-epoxidation-cyclization strategy for ladder THP synthesis

Author keywords

[No Author keywords available]

Indexed keywords

POLYETHER DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; EPOXIDE; ETHER DERIVATIVE; PYRAN DERIVATIVE;

EID: 0141853163     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0347040     Document Type: Article
Times cited : (70)

References (52)
  • 1
    • 0021860657 scopus 로고
    • (a) Nakanishi, K. Toxicon 1985, 23, 473-479.
    • (1985) Toxicon , vol.23 , pp. 473-479
    • Nakanishi, K.1
  • 5
    • 0000563379 scopus 로고    scopus 로고
    • Efforts of dozens of research groups in this area have been the subject of several recent reviews: (a) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953-1980. (b) Mori, Y. Chem. Eur. J. 1997, 3, 849-852. (c) Marmsäter, F. P.; West, F. G. Chem. Eur. J. 2002, 8, 4347-4353. (d) Hirama, M., Rainier, J. D., Eds. Tetrahedron Symposium-in-Print 90 2002, 58, 1779-2040.
    • (1995) Chem. Rev. , vol.95 , pp. 1953-1980
    • Alvarez, E.1    Candenas, M.-L.2    Pérez, R.3    Ravelo, J.L.4    Martín, J.D.5
  • 6
    • 0030944753 scopus 로고    scopus 로고
    • Efforts of dozens of research groups in this area have been the subject of several recent reviews: (a) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953-1980. (b) Mori, Y. Chem. Eur. J. 1997, 3, 849-852. (c) Marmsäter, F. P.; West, F. G. Chem. Eur. J. 2002, 8, 4347-4353. (d) Hirama, M., Rainier, J. D., Eds. Tetrahedron Symposium-in-Print 90 2002, 58, 1779-2040.
    • (1997) Chem. Eur. J. , vol.3 , pp. 849-852
    • Mori, Y.1
  • 7
    • 0000563379 scopus 로고    scopus 로고
    • Efforts of dozens of research groups in this area have been the subject of several recent reviews: (a) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953-1980. (b) Mori, Y. Chem. Eur. J. 1997, 3, 849-852. (c) Marmsäter, F. P.; West, F. G. Chem. Eur. J. 2002, 8, 4347-4353. (d) Hirama, M., Rainier, J. D., Eds. Tetrahedron Symposium-in-Print 90 2002, 58, 1779-2040.
    • (2002) Chem. Eur. J. , vol.8 , pp. 4347-4353
    • Marmsäter, F.P.1    West, F.G.2
  • 8
    • 0000563379 scopus 로고    scopus 로고
    • Efforts of dozens of research groups in this area have been the subject of several recent reviews: (a) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953-1980. (b) Mori, Y. Chem. Eur. J. 1997, 3, 849-852. (c) Marmsäter, F. P.; West, F. G. Chem. Eur. J. 2002, 8, 4347-4353. (d) Hirama, M., Rainier, J. D., Eds. Tetrahedron Symposium-in-Print 90 2002, 58, 1779-2040.
    • (2002) Tetrahedron Symposium-in-Print 90 , vol.58 , pp. 1779-2040
    • Hirama, M.1    Rainier, J.D.2
  • 14
    • 0012417391 scopus 로고
    • Ethylene and trimethylene oxides
    • Elderfield, R. C., Ed.; Wiley: New York
    • Except for epoxides with aromatic substituents (e.g., styrene oxides), whose ring-opening reactions often display different mechanistic profiles. Reviews: (a) Winstein, S.; Henderson, R. B. Ethylene and Trimethylene Oxides. In Heterocyclic Compounds; Elderfield, R. C., Ed.; Wiley: New York, 1950; Vol. 1. (b) Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737-799. (c) Wohl, R. A. Chimia 1974, 28, 1-5.
    • (1950) Heterocyclic Compounds , vol.1
    • Winstein, S.1    Henderson, R.B.2
  • 15
    • 33947470048 scopus 로고
    • Except for epoxides with aromatic substituents (e.g., styrene oxides), whose ring-opening reactions often display different mechanistic profiles. Reviews: (a) Winstein, S.; Henderson, R. B. Ethylene and Trimethylene Oxides. In Heterocyclic Compounds; Elderfield, R. C., Ed.; Wiley: New York, 1950; Vol. 1. (b) Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737-799. (c) Wohl, R. A. Chimia 1974, 28, 1-5.
    • (1959) Chem. Rev. , vol.59 , pp. 737-799
    • Parker, R.E.1    Isaacs, N.S.2
  • 16
    • 0002527644 scopus 로고
    • (c) Wohl, R. A. Chimia 1974, 28, 1-5.
    • (1974) Chimia , vol.28 , pp. 1-5
    • Wohl, R.A.1
  • 20
    • 0027922048 scopus 로고
    • Catalytic antibody approach. THP: (a) Janda, K. D.; Shevlin, C. G.; Lerner, R. A. Science 1993, 259, 490-493. (b) Na, J.; Houk, K. N.; Shevlin, C. G.; Janda, K. D.; Lerner, R. A. J. Am. Chem. Soc. 1993, 115, 8453-8454. Oxepane: (c) Janda, K. D.; Shevlin, C. G.; Lerner, R. A. J. Am. Chem. Soc. 1995, 117, 2659-2660.
    • (1993) Science , vol.259 , pp. 490-493
    • Janda, K.D.1    Shevlin, C.G.2    Lerner, R.A.3
  • 21
    • 0000778698 scopus 로고
    • Catalytic antibody approach. THP: (a) Janda, K. D.; Shevlin, C. G.; Lerner, R. A. Science 1993, 259, 490-493. (b) Na, J.; Houk, K. N.; Shevlin, C. G.; Janda, K. D.; Lerner, R. A. J. Am. Chem. Soc. 1993, 115, 8453-8454. Oxepane: (c) Janda, K. D.; Shevlin, C. G.; Lerner, R. A. J. Am. Chem. Soc. 1995, 117, 2659-2660.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 8453-8454
    • Na, J.1    Houk, K.N.2    Shevlin, C.G.3    Janda, K.D.4    Lerner, R.A.5
  • 22
    • 0028913329 scopus 로고
    • Catalytic antibody approach. THP: (a) Janda, K. D.; Shevlin, C. G.; Lerner, R. A. Science 1993, 259, 490-493. (b) Na, J.; Houk, K. N.; Shevlin, C. G.; Janda, K. D.; Lerner, R. A. J. Am. Chem. Soc. 1993, 115, 8453-8454. Oxepane: (c) Janda, K. D.; Shevlin, C. G.; Lerner, R. A. J. Am. Chem. Soc. 1995, 117, 2659-2660.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 2659-2660
    • Janda, K.D.1    Shevlin, C.G.2    Lerner, R.A.3
  • 30
    • 0001065270 scopus 로고
    • Total or formal synthesis of hemibrevetoxin: (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y. J. Am. Chem. Soc. 1992, 114, 7935-7936. (b) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558-3575. (c) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777-5780. (d) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365-6368. (e) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. (f) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209. (g) Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597-6606. (h) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380-1386. (i) Holland, J. M.; Lewis, M.; Nelson, A. J. Org. Chem. 2003, 68, 747-753.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7935-7936
    • Nicolaou, K.C.1    Reddy, K.R.2    Skokotas, G.3    Sato, F.4    Xiao, X.-Y.5
  • 31
    • 0001339910 scopus 로고
    • Total or formal synthesis of hemibrevetoxin: (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y. J. Am. Chem. Soc. 1992, 114, 7935-7936. (b) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558-3575. (c) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777-5780. (d) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365-6368. (e) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. (f) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209. (g) Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597-6606. (h) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380-1386. (i) Holland, J. M.; Lewis, M.; Nelson, A. J. Org. Chem. 2003, 68, 747-753.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 3558-3575
    • Nicolaou, K.C.1    Reddy, K.R.2    Skokotas, G.3    Sato, F.4    Xiao, X.-Y.5    Hwang, C.-K.6
  • 32
    • 85047672305 scopus 로고
    • Total or formal synthesis of hemibrevetoxin: (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y. J. Am. Chem. Soc. 1992, 114, 7935-7936. (b) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558-3575. (c) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777-5780. (d) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365-6368. (e) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. (f) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209. (g) Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597-6606. (h) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380-1386. (i) Holland, J. M.; Lewis, M.; Nelson, A. J. Org. Chem. 2003, 68, 747-753.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5777-5780
    • Kadota, I.1    Park, J.-Y.2    Koumura, N.3    Pollaud, G.4    Matsukawa, Y.5    Yamamoto, Y.6
  • 33
    • 0030603086 scopus 로고    scopus 로고
    • Total or formal synthesis of hemibrevetoxin: (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y. J. Am. Chem. Soc. 1992, 114, 7935-7936. (b) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558-3575. (c) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777-5780. (d) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365-6368. (e) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. (f) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209. (g) Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597-6606. (h) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380-1386. (i) Holland, J. M.; Lewis, M.; Nelson, A. J. Org. Chem. 2003, 68, 747-753.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6365-6368
    • Morimoto, M.1    Matsukura, H.2    Nakata, T.3
  • 34
    • 0030999573 scopus 로고    scopus 로고
    • Total or formal synthesis of hemibrevetoxin: (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y. J. Am. Chem. Soc. 1992, 114, 7935-7936. (b) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558-3575. (c) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777-5780. (d) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365-6368. (e) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. (f) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209. (g) Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597-6606. (h) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380-1386. (i) Holland, J. M.; Lewis, M.; Nelson, A. J. Org. Chem. 2003, 68, 747-753.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 4557-4558
    • Mori, Y.1    Yaegashi, K.2    Furukawa, H.3
  • 35
    • 0032483567 scopus 로고    scopus 로고
    • Total or formal synthesis of hemibrevetoxin: (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y. J. Am. Chem. Soc. 1992, 114, 7935-7936. (b) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558-3575. (c) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777-5780. (d) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365-6368. (e) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. (f) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209. (g) Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597-6606. (h) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380-1386. (i) Holland, J. M.; Lewis, M.; Nelson, A. J. Org. Chem. 2003, 68, 747-753.
    • (1998) J. Org. Chem. , vol.63 , pp. 6200-6209
    • Mori, Y.1    Yaegashi, K.2    Furukawa, H.3
  • 36
    • 0000713605 scopus 로고    scopus 로고
    • Total or formal synthesis of hemibrevetoxin: (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y. J. Am. Chem. Soc. 1992, 114, 7935-7936. (b) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558-3575. (c) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777-5780. (d) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365-6368. (e) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. (f) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209. (g) Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597-6606. (h) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380-1386. (i) Holland, J. M.; Lewis, M.; Nelson, A. J. Org. Chem. 2003, 68, 747-753.
    • (1998) J. Org. Chem. , vol.63 , pp. 6597-6606
    • Kadota, I.1    Yamamoto, Y.2
  • 37
    • 0035936738 scopus 로고    scopus 로고
    • Total or formal synthesis of hemibrevetoxin: (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y. J. Am. Chem. Soc. 1992, 114, 7935-7936. (b) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558-3575. (c) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777-5780. (d) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365-6368. (e) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. (f) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209. (g) Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597-6606. (h) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380-1386. (i) Holland, J. M.; Lewis, M.; Nelson, A. J. Org. Chem. 2003, 68, 747-753.
    • (2001) J. Org. Chem. , vol.66 , pp. 1380-1386
    • Rainier, J.D.1    Allwein, S.P.2    Cox, J.M.3
  • 38
    • 0346668206 scopus 로고    scopus 로고
    • Total or formal synthesis of hemibrevetoxin: (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y. J. Am. Chem. Soc. 1992, 114, 7935-7936. (b) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558-3575. (c) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777-5780. (d) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365-6368. (e) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. (f) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200-6209. (g) Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597-6606. (h) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380-1386. (i) Holland, J. M.; Lewis, M.; Nelson, A. J. Org. Chem. 2003, 68, 747-753.
    • (2003) J. Org. Chem. , vol.68 , pp. 747-753
    • Holland, J.M.1    Lewis, M.2    Nelson, A.3
  • 44
    • 0002348766 scopus 로고
    • α,β-Epoxysilanes
    • Larson, G. L., Ed.; JAI Press: Greenwich, CT
    • (d) Review: Hurdlik, P. F.; Hurdlik, A. M. α,β-Epoxysilanes. In Advances in Silicon Chemistry; Larson, G. L., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 1-89.
    • (1993) Advances in Silicon Chemistry , vol.2 , pp. 1-89
    • Hurdlik, P.F.1    Hurdlik, A.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.