메뉴 건너뛰기




Volumn 68, Issue 13, 2003, Pages 5274-5285

Preparation of perhydroisoquinolines via the intramolecular Diels-Alder reaction of N-3,5-hexadienoyl ethyl acrylimidates: A formal synthesis of (±)-reserpine

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION;

EID: 0037533940     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0341362     Document Type: Article
Times cited : (27)

References (56)
  • 8
    • 0002701128 scopus 로고    scopus 로고
    • Pearson, W. H., Ed.; JAI Press: Greenwich, CT
    • For reviews of synthetic entries to the yohimbine alkaloids, see: (a) Aube, J.; Ghosh, S. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, pp 99-150. (b) Szantay, C.; Honty, K. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; John Wiley & Sons: Chichester, 1994; Vol. 25, pp 161-216. (d) Baxter, E. W.; Mariano, P. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Springer- Verlag: New York, 1992; Vol. 8, pp 197-319. (d) Szantay, C.; Blasko, G.; Honty, K.; Dornyei, G. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1986; Vol. 27, pp 131-268.
    • (1996) Advances in Heterocyclic Natural Product Synthesis , vol.3 , pp. 99-150
    • Aube, J.1    Ghosh, S.2
  • 9
    • 0000231016 scopus 로고
    • Saxton, J.E., Ed.; John Wiley & Sons: Chichester
    • For reviews of synthetic entries to the yohimbine alkaloids, see: (a) Aube, J.; Ghosh, S. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, pp 99-150. (b) Szantay, C.; Honty, K. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; John Wiley & Sons: Chichester, 1994; Vol. 25, pp 161-216. (d) Baxter, E. W.; Mariano, P. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Springer- Verlag: New York, 1992; Vol. 8, pp 197-319. (d) Szantay, C.; Blasko, G.; Honty, K.; Dornyei, G. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1986; Vol. 27, pp 131-268.
    • (1994) Monoterpenoid Indole Alkaloids , vol.25 , pp. 161-216
    • Szantay, C.1    Honty, K.2
  • 10
    • 0001330381 scopus 로고
    • Pelletier, S.W., Ed.; Springer-Verlag: New York
    • For reviews of synthetic entries to the yohimbine alkaloids, see: (a) Aube, J.; Ghosh, S. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, pp 99-150. (b) Szantay, C.; Honty, K. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; John Wiley & Sons: Chichester, 1994; Vol. 25, pp 161-216. (d) Baxter, E. W.; Mariano, P. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Springer- Verlag: New York, 1992; Vol. 8, pp 197-319. (d) Szantay, C.; Blasko, G.; Honty, K.; Dornyei, G. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1986; Vol. 27, pp 131-268.
    • (1992) Alkaloids: Chemical and Biological Perspectives , vol.8 , pp. 197-319
    • Baxter, E.W.1    Mariano, P.S.2
  • 11
    • 77957077956 scopus 로고
    • Brossi, A., Ed.; Academic Press: Orlando
    • For reviews of synthetic entries to the yohimbine alkaloids, see: (a) Aube, J.; Ghosh, S. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, pp 99-150. (b) Szantay, C.; Honty, K. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; John Wiley & Sons: Chichester, 1994; Vol. 25, pp 161-216. (d) Baxter, E. W.; Mariano, P. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Springer- Verlag: New York, 1992; Vol. 8, pp 197-319. (d) Szantay, C.; Blasko, G.; Honty, K.; Dornyei, G. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1986; Vol. 27, pp 131-268.
    • (1986) The Alkaloids , vol.27 , pp. 131-268
    • Szantay, C.1    Blasko, G.2    Honty, K.3    Dornyei, G.4
  • 12
    • 0000651188 scopus 로고
    • For total syntheses ofreserpine, see: (a) Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023-2025. (b) Woodward, R. B.; Bader, F. E.; Bickel, H.; Kierstead, R. W. Tetrahedron 1958, 2, 1-57.(c) Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6404-6408. (d) Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157-6159. (e) Wender, P. A.; Schaus, J. M.; White, A. W. Hetereocycles 1987, 25, 263-270. (f) Martin, S. F.; Grzejszczak, S.; Rüeger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072. (g) Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124-6136. (h) Stork, G. Pure Appl. Chem. 1989, 61, 439-442. (i) Hanessian, S.; Pan, J. W.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem, 1997, 62, 465-473.
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 2023-2025
    • Woodward, R.B.1    Bader, F.E.2    Bickel, H.3    Frey, A.J.4    Kierstead, R.W.5
  • 13
    • 0000016992 scopus 로고
    • For total syntheses ofreserpine, see: (a) Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023-2025. (b) Woodward, R. B.; Bader, F. E.; Bickel, H.; Kierstead, R. W. Tetrahedron 1958, 2, 1-57.(c) Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6404-6408. (d) Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157-6159. (e) Wender, P. A.; Schaus, J. M.; White, A. W. Hetereocycles 1987, 25, 263-270. (f) Martin, S. F.; Grzejszczak, S.; Rüeger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072. (g) Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124-6136. (h) Stork, G. Pure Appl. Chem. 1989, 61, 439-442. (i) Hanessian, S.; Pan, J. W.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem, 1997, 62, 465-473.
    • (1958) Tetrahedron , vol.2 , pp. 1-57
    • Woodward, R.B.1    Bader, F.E.2    Bickel, H.3    Kierstead, R.W.4
  • 14
    • 0018568811 scopus 로고
    • For total syntheses ofreserpine, see: (a) Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023-2025. (b) Woodward, R. B.; Bader, F. E.; Bickel, H.; Kierstead, R. W. Tetrahedron 1958, 2, 1-57.(c) Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6404-6408. (d) Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157-6159. (e) Wender, P. A.; Schaus, J. M.; White, A. W. Hetereocycles 1987, 25, 263-270. (f) Martin, S. F.; Grzejszczak, S.; Rüeger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072. (g) Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124-6136. (h) Stork, G. Pure Appl. Chem. 1989, 61, 439-442. (i) Hanessian, S.; Pan, J. W.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem, 1997, 62, 465-473.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 6404-6408
    • Pearlman, B.A.1
  • 15
    • 0019129927 scopus 로고
    • For total syntheses ofreserpine, see: (a) Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023-2025. (b) Woodward, R. B.; Bader, F. E.; Bickel, H.; Kierstead, R. W. Tetrahedron 1958, 2, 1-57.(c) Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6404-6408. (d) Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157-6159. (e) Wender, P. A.; Schaus, J. M.; White, A. W. Hetereocycles 1987, 25, 263-270. (f) Martin, S. F.; Grzejszczak, S.; Rüeger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072. (g) Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124-6136. (h) Stork, G. Pure Appl. Chem. 1989, 61, 439-442. (i) Hanessian, S.; Pan, J. W.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem, 1997, 62, 465-473.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 6157-6159
    • Wender, P.A.1    Schaus, J.M.2    White, A.W.3
  • 16
    • 28044435882 scopus 로고
    • For total syntheses ofreserpine, see: (a) Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023-2025. (b) Woodward, R. B.; Bader, F. E.; Bickel, H.; Kierstead, R. W. Tetrahedron 1958, 2, 1-57.(c) Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6404-6408. (d) Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157-6159. (e) Wender, P. A.; Schaus, J. M.; White, A. W. Hetereocycles 1987, 25, 263-270. (f) Martin, S. F.; Grzejszczak, S.; Rüeger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072. (g) Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124-6136. (h) Stork, G. Pure Appl. Chem. 1989, 61, 439-442. (i) Hanessian, S.; Pan, J. W.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem, 1997, 62, 465-473.
    • (1987) Hetereocycles , vol.25 , pp. 263-270
    • Wender, P.A.1    Schaus, J.M.2    White, A.W.3
  • 17
    • 0021970407 scopus 로고
    • For total syntheses ofreserpine, see: (a) Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023-2025. (b) Woodward, R. B.; Bader, F. E.; Bickel, H.; Kierstead, R. W. Tetrahedron 1958, 2, 1-57.(c) Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6404-6408. (d) Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157-6159. (e) Wender, P. A.; Schaus, J. M.; White, A. W. Hetereocycles 1987, 25, 263-270. (f) Martin, S. F.; Grzejszczak, S.; Rüeger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072. (g) Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124-6136. (h) Stork, G. Pure Appl. Chem. 1989, 61, 439-442. (i) Hanessian, S.; Pan, J. W.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem, 1997, 62, 465-473.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 4072
    • Martin, S.F.1    Grzejszczak, S.2    Rüeger, H.3    Williamson, S.A.4
  • 18
    • 0023231077 scopus 로고
    • For total syntheses ofreserpine, see: (a) Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023-2025. (b) Woodward, R. B.; Bader, F. E.; Bickel, H.; Kierstead, R. W. Tetrahedron 1958, 2, 1-57.(c) Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6404-6408. (d) Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157-6159. (e) Wender, P. A.; Schaus, J. M.; White, A. W. Hetereocycles 1987, 25, 263-270. (f) Martin, S. F.; Grzejszczak, S.; Rüeger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072. (g) Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124-6136. (h) Stork, G. Pure Appl. Chem. 1989, 61, 439-442. (i) Hanessian, S.; Pan, J. W.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem, 1997, 62, 465-473.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 6124-6136
    • Martin, S.F.1    Rüeger, H.2    Williamson, S.A.3    Grzejszczak, S.4
  • 19
    • 0000999169 scopus 로고
    • For total syntheses ofreserpine, see: (a) Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023-2025. (b) Woodward, R. B.; Bader, F. E.; Bickel, H.; Kierstead, R. W. Tetrahedron 1958, 2, 1-57.(c) Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6404-6408. (d) Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157-6159. (e) Wender, P. A.; Schaus, J. M.; White, A. W. Hetereocycles 1987, 25, 263-270. (f) Martin, S. F.; Grzejszczak, S.; Rüeger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072. (g) Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124-6136. (h) Stork, G. Pure Appl. Chem. 1989, 61, 439-442. (i) Hanessian, S.; Pan, J. W.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem, 1997, 62, 465-473.
    • (1989) Pure Appl. Chem. , vol.61 , pp. 439-442
    • Stork, G.1
  • 20
    • 0031029295 scopus 로고    scopus 로고
    • For total syntheses ofreserpine, see: (a) Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023-2025. (b) Woodward, R. B.; Bader, F. E.; Bickel, H.; Kierstead, R. W. Tetrahedron 1958, 2, 1-57.(c) Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6404-6408. (d) Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157-6159. (e) Wender, P. A.; Schaus, J. M.; White, A. W. Hetereocycles 1987, 25, 263-270. (f) Martin, S. F.; Grzejszczak, S.; Rüeger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072. (g) Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124-6136. (h) Stork, G. Pure Appl. Chem. 1989, 61, 439-442. (i) Hanessian, S.; Pan, J. W.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem, 1997, 62, 465-473.
    • (1997) J. Org. Chem. , vol.62 , pp. 465-473
    • Hanessian, S.1    Pan, J.W.2    Carnell, A.3    Bouchard, H.4    Lesage, L.5
  • 43
    • 0037691334 scopus 로고
    • Ph.D. Dissertation, University of California, Irvine
    • Gutierrez, A. J. Ph.D. Dissertation, University of California, Irvine, 1990.
    • (1990)
    • Gutierrez, A.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.