메뉴 건너뛰기




Volumn 82, Issue 2, 2004, Pages 375-385

Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization - Electrophilic aromatic substitution

Author keywords

Domino process; Electrophilic aromatic substitution; Lewis acid; Nazarov cyclization

Indexed keywords

ALDEHYDES; ELECTRON TRAPS; LOW TEMPERATURE EFFECTS; SUBSTITUTION REACTIONS; TITANIUM COMPOUNDS;

EID: 2342593924     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v03-203     Document Type: Article
Times cited : (28)

References (58)
  • 1
    • 7044235263 scopus 로고    scopus 로고
    • Reviews: (a) L.F. Tietze. Chem. Rev. 96, 115 (1996); (b) G. Poli, G. Giambastiani, and A. Heumann. Tetrahedron, 56, 5959 (2000); (c) L.F. Tietze and A. Modi. Med. Res. Rev. 20, 304 (2000); (d) A. Padwa. Pure Appl. Chem. 75, 47 (2003); (e) K.C. Nicolaou, T. Montagnon, and S.A. Snyder. Chem. Commun. 551 (2003).
    • (1996) Chem. Rev. , vol.96 , pp. 115
    • Tietze, L.F.1
  • 2
    • 0034637529 scopus 로고    scopus 로고
    • Reviews: (a) L.F. Tietze. Chem. Rev. 96, 115 (1996); (b) G. Poli, G. Giambastiani, and A. Heumann. Tetrahedron, 56, 5959 (2000); (c) L.F. Tietze and A. Modi. Med. Res. Rev. 20, 304 (2000); (d) A. Padwa. Pure Appl. Chem. 75, 47 (2003); (e) K.C. Nicolaou, T. Montagnon, and S.A. Snyder. Chem. Commun. 551 (2003).
    • (2000) Tetrahedron , vol.56 , pp. 5959
    • Poli, G.1    Giambastiani, G.2    Heumann, A.3
  • 3
    • 0033947531 scopus 로고    scopus 로고
    • Reviews: (a) L.F. Tietze. Chem. Rev. 96, 115 (1996); (b) G. Poli, G. Giambastiani, and A. Heumann. Tetrahedron, 56, 5959 (2000); (c) L.F. Tietze and A. Modi. Med. Res. Rev. 20, 304 (2000); (d) A. Padwa. Pure Appl. Chem. 75, 47 (2003); (e) K.C. Nicolaou, T. Montagnon, and S.A. Snyder. Chem. Commun. 551 (2003).
    • (2000) Med. Res. Rev. , vol.20 , pp. 304
    • Tietze, L.F.1    Modi, A.2
  • 4
    • 0037221146 scopus 로고    scopus 로고
    • Reviews: (a) L.F. Tietze. Chem. Rev. 96, 115 (1996); (b) G. Poli, G. Giambastiani, and A. Heumann. Tetrahedron, 56, 5959 (2000); (c) L.F. Tietze and A. Modi. Med. Res. Rev. 20, 304 (2000); (d) A. Padwa. Pure Appl. Chem. 75, 47 (2003); (e) K.C. Nicolaou, T. Montagnon, and S.A. Snyder. Chem. Commun. 551 (2003).
    • (2003) Pure Appl. Chem. , vol.75 , pp. 47
    • Padwa, A.1
  • 5
    • 0037423972 scopus 로고    scopus 로고
    • Reviews: (a) L.F. Tietze. Chem. Rev. 96, 115 (1996); (b) G. Poli, G. Giambastiani, and A. Heumann. Tetrahedron, 56, 5959 (2000); (c) L.F. Tietze and A. Modi. Med. Res. Rev. 20, 304 (2000); (d) A. Padwa. Pure Appl. Chem. 75, 47 (2003); (e) K.C. Nicolaou, T. Montagnon, and S.A. Snyder. Chem. Commun. 551 (2003).
    • (2003) Chem. Commun. , pp. 551
    • Nicolaou, K.C.1    Montagnon, T.2    Snyder, S.A.3
  • 6
    • 0001992172 scopus 로고
    • N.Y.
    • Reviews: (a) K.L. Habermas, S.E. Denmark, and T.K. Jones. Org. React. (N.Y.), 45, 1 (1994); (b) S.E. Denmark. In Comprehensive organic synthesis. Vol. 5. Edited by B.M. Trost and I. Fleming. Pergamon, Oxford. 1991. pp. 751-784.
    • (1994) Org. React. , vol.45 , pp. 1
    • Habermas, K.L.1    Denmark, S.E.2    Jones, T.K.3
  • 7
    • 0000646877 scopus 로고
    • Edited by B.M. Trost and I. Fleming. Pergamon, Oxford
    • Reviews: (a) K.L. Habermas, S.E. Denmark, and T.K. Jones. Org. React. (N.Y.), 45, 1 (1994); (b) S.E. Denmark. In Comprehensive organic synthesis. Vol. 5. Edited by B.M. Trost and I. Fleming. Pergamon, Oxford. 1991. pp. 751-784.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 751-784
    • Denmark, S.E.1
  • 18
    • 0033952825 scopus 로고    scopus 로고
    • Isolation: (a) K.D. Wellington, R.C. Cambie, P.S. Rutledge, and P.R. Bergquist J. Nat. Prod. 63, 79 (2000); Synthesis: (b) K.C. Nicolaou, D. Gray, and J.S. Tae. Angew. Chem. Int Ed. 40, 3675 (2001); (c) K.C. Nicolaou, D. Gray, and J.S. Tae. Angew. Chem. Int. Ed. 40, 3679 (2001).
    • (2000) J. Nat. Prod. , vol.63 , pp. 79
    • Wellington, K.D.1    Cambie, R.C.2    Rutledge, P.S.3    Bergquist, P.R.4
  • 19
    • 0035476435 scopus 로고    scopus 로고
    • Isolation: (a) K.D. Wellington, R.C. Cambie, P.S. Rutledge, and P.R. Bergquist J. Nat. Prod. 63, 79 (2000); Synthesis: (b) K.C. Nicolaou, D. Gray, and J.S. Tae. Angew. Chem. Int Ed. 40, 3675 (2001); (c) K.C. Nicolaou, D. Gray, and J.S. Tae. Angew. Chem. Int. Ed. 40, 3679 (2001).
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3675
    • Nicolaou, K.C.1    Gray, D.2    Tae, J.S.3
  • 20
    • 0035476828 scopus 로고    scopus 로고
    • Isolation: (a) K.D. Wellington, R.C. Cambie, P.S. Rutledge, and P.R. Bergquist J. Nat. Prod. 63, 79 (2000); Synthesis: (b) K.C. Nicolaou, D. Gray, and J.S. Tae. Angew. Chem. Int Ed. 40, 3675 (2001); (c) K.C. Nicolaou, D. Gray, and J.S. Tae. Angew. Chem. Int. Ed. 40, 3679 (2001).
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3679
    • Nicolaou, K.C.1    Gray, D.2    Tae, J.S.3
  • 25
    • 4243952009 scopus 로고
    • Previous syntheses of 9d: (a) P. Baeckstroem, S. Okecha, N. De Silva, D. Wijekoon, and T. Norin. Acta Chem. Scand. Ser. B, B36, 31 (1982); (b) R. Baker, N. Ekanayake, and S.A. Johnson. J. Chem. Res. Synop. 74 (1983); (c) S. Bernasconi, M. Colombo, G. Jommi, and M. Sisti. Gazz. Chim. Ital. 116, 69 (1986); (d) I. Bock, H. Bornowski, A. Ranft, and H. Theis. Tetrahedron 46, 1199 (1990); (e) M. Nishizawa, H. Takenaka, T. Kohno, H. Takao, and H. Yamada. Chem. Pharm. Bull. 41, 791 (1993); (f) D.K. Barma, A. Kundu, R. Baati, C. Mioskowski, and J.R. Falck. Org. Lett. 4, 1387 (2002).
    • (1982) Acta Chem. Scand. Ser. B , vol.B36 , pp. 31
    • Baeckstroem, P.1    Okecha, S.2    De Silva, N.3    Wijekoon, D.4    Norin, T.5
  • 26
    • 84917847133 scopus 로고
    • Previous syntheses of 9d: (a) P. Baeckstroem, S. Okecha, N. De Silva, D. Wijekoon, and T. Norin. Acta Chem. Scand. Ser. B, B36, 31 (1982); (b) R. Baker, N. Ekanayake, and S.A. Johnson. J. Chem. Res. Synop. 74 (1983); (c) S. Bernasconi, M. Colombo, G. Jommi, and M. Sisti. Gazz. Chim. Ital. 116, 69 (1986); (d) I. Bock, H. Bornowski, A. Ranft, and H. Theis. Tetrahedron 46, 1199 (1990); (e) M. Nishizawa, H. Takenaka, T. Kohno, H. Takao, and H. Yamada. Chem. Pharm. Bull. 41, 791 (1993); (f) D.K. Barma, A. Kundu, R. Baati, C. Mioskowski, and J.R. Falck. Org. Lett. 4, 1387 (2002).
    • (1983) J. Chem. Res. Synop. , pp. 74
    • Baker, R.1    Ekanayake, N.2    Johnson, S.A.3
  • 27
    • 0006971269 scopus 로고
    • Previous syntheses of 9d: (a) P. Baeckstroem, S. Okecha, N. De Silva, D. Wijekoon, and T. Norin. Acta Chem. Scand. Ser. B, B36, 31 (1982); (b) R. Baker, N. Ekanayake, and S.A. Johnson. J. Chem. Res. Synop. 74 (1983); (c) S. Bernasconi, M. Colombo, G. Jommi, and M. Sisti. Gazz. Chim. Ital. 116, 69 (1986); (d) I. Bock, H. Bornowski, A. Ranft, and H. Theis. Tetrahedron 46, 1199 (1990); (e) M. Nishizawa, H. Takenaka, T. Kohno, H. Takao, and H. Yamada. Chem. Pharm. Bull. 41, 791 (1993); (f) D.K. Barma, A. Kundu, R. Baati, C. Mioskowski, and J.R. Falck. Org. Lett. 4, 1387 (2002).
    • (1986) Gazz. Chim. Ital. , vol.116 , pp. 69
    • Bernasconi, S.1    Colombo, M.2    Jommi, G.3    Sisti, M.4
  • 28
    • 0001228428 scopus 로고
    • Previous syntheses of 9d: (a) P. Baeckstroem, S. Okecha, N. De Silva, D. Wijekoon, and T. Norin. Acta Chem. Scand. Ser. B, B36, 31 (1982); (b) R. Baker, N. Ekanayake, and S.A. Johnson. J. Chem. Res. Synop. 74 (1983); (c) S. Bernasconi, M. Colombo, G. Jommi, and M. Sisti. Gazz. Chim. Ital. 116, 69 (1986); (d) I. Bock, H. Bornowski, A. Ranft, and H. Theis. Tetrahedron 46, 1199 (1990); (e) M. Nishizawa, H. Takenaka, T. Kohno, H. Takao, and H. Yamada. Chem. Pharm. Bull. 41, 791 (1993); (f) D.K. Barma, A. Kundu, R. Baati, C. Mioskowski, and J.R. Falck. Org. Lett. 4, 1387 (2002).
    • (1990) Tetrahedron , vol.46 , pp. 1199
    • Bock, I.1    Bornowski, H.2    Ranft, A.3    Theis, H.4
  • 29
    • 0027190483 scopus 로고
    • Previous syntheses of 9d: (a) P. Baeckstroem, S. Okecha, N. De Silva, D. Wijekoon, and T. Norin. Acta Chem. Scand. Ser. B, B36, 31 (1982); (b) R. Baker, N. Ekanayake, and S.A. Johnson. J. Chem. Res. Synop. 74 (1983); (c) S. Bernasconi, M. Colombo, G. Jommi, and M. Sisti. Gazz. Chim. Ital. 116, 69 (1986); (d) I. Bock, H. Bornowski, A. Ranft, and H. Theis. Tetrahedron 46, 1199 (1990); (e) M. Nishizawa, H. Takenaka, T. Kohno, H. Takao, and H. Yamada. Chem. Pharm. Bull. 41, 791 (1993); (f) D.K. Barma, A. Kundu, R. Baati, C. Mioskowski, and J.R. Falck. Org. Lett. 4, 1387 (2002).
    • (1993) Chem. Pharm. Bull. , vol.41 , pp. 791
    • Nishizawa, M.1    Takenaka, H.2    Kohno, T.3    Takao, H.4    Yamada, H.5
  • 30
    • 0037129418 scopus 로고    scopus 로고
    • Previous syntheses of 9d: (a) P. Baeckstroem, S. Okecha, N. De Silva, D. Wijekoon, and T. Norin. Acta Chem. Scand. Ser. B, B36, 31 (1982); (b) R. Baker, N. Ekanayake, and S.A. Johnson. J. Chem. Res. Synop. 74 (1983); (c) S. Bernasconi, M. Colombo, G. Jommi, and M. Sisti. Gazz. Chim. Ital. 116, 69 (1986); (d) I. Bock, H. Bornowski, A. Ranft, and H. Theis. Tetrahedron 46, 1199 (1990); (e) M. Nishizawa, H. Takenaka, T. Kohno, H. Takao, and H. Yamada. Chem. Pharm. Bull. 41, 791 (1993); (f) D.K. Barma, A. Kundu, R. Baati, C. Mioskowski, and J.R. Falck. Org. Lett. 4, 1387 (2002).
    • (2002) Org. Lett. , vol.4 , pp. 1387
    • Barma, D.K.1    Kundu, A.2    Baati, R.3    Mioskowski, C.4    Falck, J.R.5
  • 31
    • 0000478319 scopus 로고
    • N.Y.
    • Reviews: (a) R.H. Shapiro. Org. React. (N.Y.), 23, 405 (1976); (b) R.M. Adlington and A.G.M. Barrett. Acc. Chem. Res. 16, 55 (1983); Trisyl hydrazones: (c) N.J. Cusack, C.B. Reese, A.C. Risius, and B. Roozpeikar. Tetrahedron, 32, 2157 (1976).
    • (1976) Org. React. , vol.23 , pp. 405
    • Shapiro, R.H.1
  • 32
    • 0001930675 scopus 로고
    • Reviews: (a) R.H. Shapiro. Org. React. (N.Y.), 23, 405 (1976); (b) R.M. Adlington and A.G.M. Barrett. Acc. Chem. Res. 16, 55 (1983); Trisyl hydrazones: (c) N.J. Cusack, C.B. Reese, A.C. Risius, and B. Roozpeikar. Tetrahedron, 32, 2157 (1976).
    • (1983) Acc. Chem. Res. , vol.16 , pp. 55
    • Adlington, R.M.1    Barrett, A.G.M.2
  • 33
    • 0000685252 scopus 로고
    • Reviews: (a) R.H. Shapiro. Org. React. (N.Y.), 23, 405 (1976); (b) R.M. Adlington and A.G.M. Barrett. Acc. Chem. Res. 16, 55 (1983); Trisyl hydrazones: (c) N.J. Cusack, C.B. Reese, A.C. Risius, and B. Roozpeikar. Tetrahedron, 32, 2157 (1976).
    • (1976) Tetrahedron , vol.32 , pp. 2157
    • Cusack, N.J.1    Reese, C.B.2    Risius, A.C.3    Roozpeikar, B.4
  • 34
    • 84986384797 scopus 로고
    • Barium manganate is a mild and effective oxidant for the conversion of dienols to dienones: (a) S.E. Denmark and G.A. Hite. Helv. Chim. Acta, 71, 195 (1988); (b) H. Firouzabadi and E. Ghaderi. Tetrahedron Lett. 839 (1978).
    • (1988) Helv. Chim. Acta , vol.71 , pp. 195
    • Denmark, S.E.1    Hite, G.A.2
  • 35
    • 0001235197 scopus 로고
    • Barium manganate is a mild and effective oxidant for the conversion of dienols to dienones: (a) S.E. Denmark and G.A. Hite. Helv. Chim. Acta, 71, 195 (1988); (b) H. Firouzabadi and E. Ghaderi. Tetrahedron Lett. 839 (1978).
    • (1978) Tetrahedron Lett. , pp. 839
    • Firouzabadi, H.1    Ghaderi, E.2
  • 41
    • 0000942986 scopus 로고
    • Edited by Atta-ur-Rahman. Elsevier, Amsterdam
    • (b) J. Raczko and J. Jurczak. In Studies in natural product chemistry. Vol. 16. Edited by Atta-ur-Rahman. Elsevier, Amsterdam. 1995. pp. 639-685;
    • (1995) Studies in Natural Product Chemistry , vol.16 , pp. 639-685
    • Raczko, J.1    Jurczak, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.