메뉴 건너뛰기




Volumn 63, Issue 17, 1998, Pages 6007-6015

Highly Enantioselective Intermolecular Cu(I)-Catalyzed Cyclopropanation of Cyclic Enol Ethers. Asymmetric Total Synthesis of (+)-Quebrachamine

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0001509324     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9807417     Document Type: Article
Times cited : (70)

References (76)
  • 6
    • 0037599887 scopus 로고    scopus 로고
    • Helmchen, G., Hoffmann R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart E21
    • (c) Reissig, H. U. In Stereoselective Synthesis, Houben-Weyl; Helmchen, G., Hoffmann R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart 1996; E21, Vol. 5, p 3179.
    • (1996) Stereoselective Synthesis, Houben-Weyl , vol.5 , pp. 3179
    • Reissig, H.U.1
  • 11
    • 0001713095 scopus 로고    scopus 로고
    • Some recent papers: (a) Ashutosh, V. B.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (b) Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1997, 53, 9599. (c) Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Tarnai, T. Tetrahedron: Asymmetry 1997, 8, 2089. (d) Bolm, C.; Pupowicz, D. Tetrahedron Lett. 1997, 38, 7349. (e) Aggarwal, K. V.; Smith, H. W.; Jones, R.; Fieldhouse, R. Chem. Commun. 1997, 1785. (f) Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175. (g) Haddad, N.; Galili, N. Tetrahedron: Asymmetry 1997, 8, 3367. (h) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390.
    • (1997) J. Org. Chem. , vol.62 , pp. 2518
    • Ashutosh, V.B.1    Koroleva, E.B.2    Andersson, P.G.3
  • 12
    • 0030744464 scopus 로고    scopus 로고
    • Some recent papers: (a) Ashutosh, V. B.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (b) Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1997, 53, 9599. (c) Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Tarnai, T. Tetrahedron: Asymmetry 1997, 8, 2089. (d) Bolm, C.; Pupowicz, D. Tetrahedron Lett. 1997, 38, 7349. (e) Aggarwal, K. V.; Smith, H. W.; Jones, R.; Fieldhouse, R. Chem. Commun. 1997, 1785. (f) Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175. (g) Haddad, N.; Galili, N. Tetrahedron: Asymmetry 1997, 8, 3367. (h) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390.
    • (1997) Tetrahedron , vol.53 , pp. 9599
    • Ichiyanagi, T.1    Shimizu, M.2    Fujisawa, T.3
  • 13
    • 0030862579 scopus 로고    scopus 로고
    • Some recent papers: (a) Ashutosh, V. B.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (b) Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1997, 53, 9599. (c) Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Tarnai, T. Tetrahedron: Asymmetry 1997, 8, 2089. (d) Bolm, C.; Pupowicz, D. Tetrahedron Lett. 1997, 38, 7349. (e) Aggarwal, K. V.; Smith, H. W.; Jones, R.; Fieldhouse, R. Chem. Commun. 1997, 1785. (f) Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175. (g) Haddad, N.; Galili, N. Tetrahedron: Asymmetry 1997, 8, 3367. (h) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 2089
    • Fraile, J.M.1    Garcia, J.I.2    Mayoral, J.A.3    Tarnai, T.4
  • 14
    • 0030770654 scopus 로고    scopus 로고
    • Some recent papers: (a) Ashutosh, V. B.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (b) Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1997, 53, 9599. (c) Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Tarnai, T. Tetrahedron: Asymmetry 1997, 8, 2089. (d) Bolm, C.; Pupowicz, D. Tetrahedron Lett. 1997, 38, 7349. (e) Aggarwal, K. V.; Smith, H. W.; Jones, R.; Fieldhouse, R. Chem. Commun. 1997, 1785. (f) Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175. (g) Haddad, N.; Galili, N. Tetrahedron: Asymmetry 1997, 8, 3367. (h) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7349
    • Bolm, C.1    Pupowicz, D.2
  • 15
    • 0002177492 scopus 로고    scopus 로고
    • Some recent papers: (a) Ashutosh, V. B.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (b) Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1997, 53, 9599. (c) Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Tarnai, T. Tetrahedron: Asymmetry 1997, 8, 2089. (d) Bolm, C.; Pupowicz, D. Tetrahedron Lett. 1997, 38, 7349. (e) Aggarwal, K. V.; Smith, H. W.; Jones, R.; Fieldhouse, R. Chem. Commun. 1997, 1785. (f) Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175. (g) Haddad, N.; Galili, N. Tetrahedron: Asymmetry 1997, 8, 3367. (h) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390.
    • (1997) Chem. Commun. , pp. 1785
    • Aggarwal, K.V.1    Smith, H.W.2    Jones, R.3    Fieldhouse, R.4
  • 16
    • 0030713072 scopus 로고    scopus 로고
    • Some recent papers: (a) Ashutosh, V. B.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (b) Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1997, 53, 9599. (c) Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Tarnai, T. Tetrahedron: Asymmetry 1997, 8, 2089. (d) Bolm, C.; Pupowicz, D. Tetrahedron Lett. 1997, 38, 7349. (e) Aggarwal, K. V.; Smith, H. W.; Jones, R.; Fieldhouse, R. Chem. Commun. 1997, 1785. (f) Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175. (g) Haddad, N.; Galili, N. Tetrahedron: Asymmetry 1997, 8, 3367. (h) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7175
    • Frauenkron, M.1    Berkessel, A.2
  • 17
    • 0030718554 scopus 로고    scopus 로고
    • Some recent papers: (a) Ashutosh, V. B.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (b) Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1997, 53, 9599. (c) Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Tarnai, T. Tetrahedron: Asymmetry 1997, 8, 2089. (d) Bolm, C.; Pupowicz, D. Tetrahedron Lett. 1997, 38, 7349. (e) Aggarwal, K. V.; Smith, H. W.; Jones, R.; Fieldhouse, R. Chem. Commun. 1997, 1785. (f) Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175. (g) Haddad, N.; Galili, N. Tetrahedron: Asymmetry 1997, 8, 3367. (h) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 3367
    • Haddad, N.1    Galili, N.2
  • 18
    • 0030989390 scopus 로고    scopus 로고
    • Some recent papers: (a) Ashutosh, V. B.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (b) Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1997, 53, 9599. (c) Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Tarnai, T. Tetrahedron: Asymmetry 1997, 8, 2089. (d) Bolm, C.; Pupowicz, D. Tetrahedron Lett. 1997, 38, 7349. (e) Aggarwal, K. V.; Smith, H. W.; Jones, R.; Fieldhouse, R. Chem. Commun. 1997, 1785. (f) Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175. (g) Haddad, N.; Galili, N. Tetrahedron: Asymmetry 1997, 8, 3367. (h) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390.
    • (1997) J. Org. Chem. , vol.62 , pp. 2337
    • Pyne, S.G.1    Dong, Z.2    Skelton, B.W.3    White, A.H.4
  • 19
    • 0001170684 scopus 로고    scopus 로고
    • Some recent papers: (a) Ashutosh, V. B.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (b) Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1997, 53, 9599. (c) Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Tarnai, T. Tetrahedron: Asymmetry 1997, 8, 2089. (d) Bolm, C.; Pupowicz, D. Tetrahedron Lett. 1997, 38, 7349. (e) Aggarwal, K. V.; Smith, H. W.; Jones, R.; Fieldhouse, R. Chem. Commun. 1997, 1785. (f) Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175. (g) Haddad, N.; Galili, N. Tetrahedron: Asymmetry 1997, 8, 3367. (h) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390.
    • (1997) J. Org. Chem. , vol.62 , pp. 3390
    • Denmark, S.E.1    O'Connor, S.P.2
  • 49
    • 0003588273 scopus 로고
    • Thieme: Stuttgart, 3.Aufl.
    • Guenther, H. In NMR-Spektroskopie; Thieme: Stuttgart, 1992; 3.Aufl., p 109.
    • (1992) NMR-Spektroskopie , pp. 109
    • Guenther, H.1
  • 53
    • 0030873573 scopus 로고    scopus 로고
    • Some recent papers concerning the total synthesis of Aspidosperma and vincamine alkaloids: (a) Schultz, A. G.; Liping, P. J. Org. Chem. 1997, 62, 6855. (b) Desmaele, D.; Mekonar, K.; D'Angelo, J. J. Org. Chem. 1997, 62, 3890. (c) Schultz, A. G.; Malachowski, W. P.; You, P. J. Org. Chem. 1997, 62, 1223.
    • (1997) J. Org. Chem. , vol.62 , pp. 6855
    • Schultz, A.G.1    Liping, P.2
  • 54
    • 0030754465 scopus 로고    scopus 로고
    • Some recent papers concerning the total synthesis of Aspidosperma and vincamine alkaloids: (a) Schultz, A. G.; Liping, P. J. Org. Chem. 1997, 62, 6855. (b) Desmaele, D.; Mekonar, K.; D'Angelo, J. J. Org. Chem. 1997, 62, 3890. (c) Schultz, A. G.; Malachowski, W. P.; You, P. J. Org. Chem. 1997, 62, 1223.
    • (1997) J. Org. Chem. , vol.62 , pp. 3890
    • Desmaele, D.1    Mekonar, K.2    D'Angelo, J.3
  • 55
    • 0030972990 scopus 로고    scopus 로고
    • Some recent papers concerning the total synthesis of Aspidosperma and vincamine alkaloids: (a) Schultz, A. G.; Liping, P. J. Org. Chem. 1997, 62, 6855. (b) Desmaele, D.; Mekonar, K.; D'Angelo, J. J. Org. Chem. 1997, 62, 3890. (c) Schultz, A. G.; Malachowski, W. P.; You, P. J. Org. Chem. 1997, 62, 1223.
    • (1997) J. Org. Chem. , vol.62 , pp. 1223
    • Schultz, A.G.1    Malachowski, W.P.2    You, P.3
  • 57
    • 33947338587 scopus 로고
    • Racemic syntheses of quebrachamine 7: (a) Kutney, J. P.; Abdurahman, N.; Le Quesne, P.; Piers, E.; Vlattas, I. J. Am. Chem. Soc. 1966, 88, 3656. (b) Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T.; Takeda, E. Tetrahedron 1983, 39, 3657. (c) Ziegler, F. E.; Kloek, J. A.; Zoretic, P. A. J. Am. Chem. Soc. 1969, 91, 2342. (d) Takano, S.; Hatakeyama, S.; Ogasawara, K. J. Am. Chem. Soc. 1976, 98, 3022. (e) Giri, V. S.; Ali, E.; Pakrashi, S. C. J. Heterocycl. Chem. 1980, 17, 1133.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 3656
    • Kutney, J.P.1    Abdurahman, N.2    Le Quesne, P.3    Piers, E.4    Vlattas, I.5
  • 58
    • 0021039588 scopus 로고
    • Racemic syntheses of quebrachamine 7: (a) Kutney, J. P.; Abdurahman, N.; Le Quesne, P.; Piers, E.; Vlattas, I. J. Am. Chem. Soc. 1966, 88, 3656. (b) Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T.; Takeda, E. Tetrahedron 1983, 39, 3657. (c) Ziegler, F. E.; Kloek, J. A.; Zoretic, P. A. J. Am. Chem. Soc. 1969, 91, 2342. (d) Takano, S.; Hatakeyama, S.; Ogasawara, K. J. Am. Chem. Soc. 1976, 98, 3022. (e) Giri, V. S.; Ali, E.; Pakrashi, S. C. J. Heterocycl. Chem. 1980, 17, 1133.
    • (1983) Tetrahedron , vol.39 , pp. 3657
    • Ban, Y.1    Yoshida, K.2    Goto, J.3    Oishi, T.4    Takeda, E.5
  • 59
    • 0000713628 scopus 로고
    • Racemic syntheses of quebrachamine 7: (a) Kutney, J. P.; Abdurahman, N.; Le Quesne, P.; Piers, E.; Vlattas, I. J. Am. Chem. Soc. 1966, 88, 3656. (b) Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T.; Takeda, E. Tetrahedron 1983, 39, 3657. (c) Ziegler, F. E.; Kloek, J. A.; Zoretic, P. A. J. Am. Chem. Soc. 1969, 91, 2342. (d) Takano, S.; Hatakeyama, S.; Ogasawara, K. J. Am. Chem. Soc. 1976, 98, 3022. (e) Giri, V. S.; Ali, E.; Pakrashi, S. C. J. Heterocycl. Chem. 1980, 17, 1133.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 2342
    • Ziegler, F.E.1    Kloek, J.A.2    Zoretic, P.A.3
  • 60
    • 0017305058 scopus 로고
    • Racemic syntheses of quebrachamine 7: (a) Kutney, J. P.; Abdurahman, N.; Le Quesne, P.; Piers, E.; Vlattas, I. J. Am. Chem. Soc. 1966, 88, 3656. (b) Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T.; Takeda, E. Tetrahedron 1983, 39, 3657. (c) Ziegler, F. E.; Kloek, J. A.; Zoretic, P. A. J. Am. Chem. Soc. 1969, 91, 2342. (d) Takano, S.; Hatakeyama, S.; Ogasawara, K. J. Am. Chem. Soc. 1976, 98, 3022. (e) Giri, V. S.; Ali, E.; Pakrashi, S. C. J. Heterocycl. Chem. 1980, 17, 1133.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 3022
    • Takano, S.1    Hatakeyama, S.2    Ogasawara, K.3
  • 61
    • 0019211319 scopus 로고
    • Racemic syntheses of quebrachamine 7: (a) Kutney, J. P.; Abdurahman, N.; Le Quesne, P.; Piers, E.; Vlattas, I. J. Am. Chem. Soc. 1966, 88, 3656. (b) Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T.; Takeda, E. Tetrahedron 1983, 39, 3657. (c) Ziegler, F. E.; Kloek, J. A.; Zoretic, P. A. J. Am. Chem. Soc. 1969, 91, 2342. (d) Takano, S.; Hatakeyama, S.; Ogasawara, K. J. Am. Chem. Soc. 1976, 98, 3022. (e) Giri, V. S.; Ali, E.; Pakrashi, S. C. J. Heterocycl. Chem. 1980, 17, 1133.
    • (1980) J. Heterocycl. Chem. , vol.17 , pp. 1133
    • Giri, V.S.1    Ali, E.2    Pakrashi, S.C.3
  • 62
    • 77957029008 scopus 로고
    • Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York
    • (a) Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17; p 199.
    • (1979) The Alkaloids , vol.17 , pp. 199
    • Cordell, G.A.1
  • 64
    • 0001908212 scopus 로고
    • Cordell, G. A., Ed.; Academic Press: New York
    • (c) Lohnasmaa, M.; Tolvanen, A. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York 1992; Vol. 42, p 1.
    • (1992) The Alkaloids , vol.42 , pp. 1
    • Lohnasmaa, M.1    Tolvanen, A.2
  • 65
    • 0023521548 scopus 로고
    • Asymmetric syntheses of quebrachamine 7: (a) Manabu, N.; Nagasawa, H.; Fuji, K. J. Am. Chem. Soc. 1987, 109, 7901. (b) Takano, S.; Chiba, K.; Yonaga, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1980, 616. (c) Takano, S.; Chiba, K.; Yonaga, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1981, 1153.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 7901
    • Manabu, N.1    Nagasawa, H.2    Fuji, K.3
  • 66
    • 37049096415 scopus 로고
    • Asymmetric syntheses of quebrachamine 7: (a) Manabu, N.; Nagasawa, H.; Fuji, K. J. Am. Chem. Soc. 1987, 109, 7901. (b) Takano, S.; Chiba, K.; Yonaga, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1980, 616. (c) Takano, S.; Chiba, K.; Yonaga, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1981, 1153.
    • (1980) J. Chem. Soc., Chem. Commun. , pp. 616
    • Takano, S.1    Chiba, K.2    Yonaga, M.3    Ogasawara, K.4
  • 67
    • 0023521548 scopus 로고
    • Asymmetric syntheses of quebrachamine 7: (a) Manabu, N.; Nagasawa, H.; Fuji, K. J. Am. Chem. Soc. 1987, 109, 7901. (b) Takano, S.; Chiba, K.; Yonaga, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1980, 616. (c) Takano, S.; Chiba, K.; Yonaga, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1981, 1153.
    • (1981) J. Chem. Soc., Chem. Commun. , pp. 1153
    • Takano, S.1    Chiba, K.2    Yonaga, M.3    Ogasawara, K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.