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Volumn 2, Issue 11, 2000, Pages 1625-1627

Regiocontrol in an Intramolecular Schmidt Reaction: Total Synthesis of (+)-Aspidospermidine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ASPIDOSPERMIDINE; DRUG DERIVATIVE; INDOLE DERIVATIVE; QUINOLINE DERIVATIVE; SPERMIDINE;

EID: 0034199893     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005913c     Document Type: Article
Times cited : (102)

References (38)
  • 8
    • 29944444144 scopus 로고    scopus 로고
    • Cordell, G. A., Ed.; Academic: New York, References to more recent work in this area include
    • For a recent review, see: (a) Saxton, J. E. In The Alkaloids', Cordell, G. A., Ed.; Academic: New York, 1998; Vol. 51, pp 1-197. References to more recent work in this area include: (b) Callaghan, O.; Lampard, C.; Kennedy, A. R.; Murphy, J. A. Tetrahedron Lett. 1999, 40, 161-164. (c) Dupont, C.; Guénard, D.; Tchertanov, L.; Thoret, S.; Guéritte, F. Bioorg. Med. Chem. 1999, 7, 2961-2969. (d) Kizil, M.; Patro, B.; Callaghan, O.; Murphy, J. A.; Hursthouse, M. B.; Hibbs, D. J. Org. Chem. 1999, 64, 7856-7862. (e) Quinn, J. F.; Bos, M. E.; Wulff, W. D. Org. Lett. 1999, 1, 161-164. (f) Urrutia, A.; Rodriguez, G. Tetrahedron Lett. 1998, 39, 4143-4146. (g) Urrutia, A.; Rodriguez, J. G. Tetrahedron 1999, 55, 11095-11108. (h) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1998, 120, 13523-13524.
    • (1998) The Alkaloids' , vol.51 , pp. 1-197
    • Saxton, J.E.1
  • 9
    • 0032888938 scopus 로고    scopus 로고
    • For a recent review, see: (a) Saxton, J. E. In The Alkaloids', Cordell, G. A., Ed.; Academic: New York, 1998; Vol. 51, pp 1-197. References to more recent work in this area include: (b) Callaghan, O.; Lampard, C.; Kennedy, A. R.; Murphy, J. A. Tetrahedron Lett. 1999, 40, 161-164. (c) Dupont, C.; Guénard, D.; Tchertanov, L.; Thoret, S.; Guéritte, F. Bioorg. Med. Chem. 1999, 7, 2961-2969. (d) Kizil, M.; Patro, B.; Callaghan, O.; Murphy, J. A.; Hursthouse, M. B.; Hibbs, D. J. Org. Chem. 1999, 64, 7856-7862. (e) Quinn, J. F.; Bos, M. E.; Wulff, W. D. Org. Lett. 1999, 1, 161-164. (f) Urrutia, A.; Rodriguez, G. Tetrahedron Lett. 1998, 39, 4143-4146. (g) Urrutia, A.; Rodriguez, J. G. Tetrahedron 1999, 55, 11095-11108. (h) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1998, 120, 13523-13524.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 161-164
    • Callaghan, O.1    Lampard, C.2    Kennedy, A.R.3    Murphy, J.A.4
  • 10
    • 0343485102 scopus 로고    scopus 로고
    • For a recent review, see: (a) Saxton, J. E. In The Alkaloids', Cordell, G. A., Ed.; Academic: New York, 1998; Vol. 51, pp 1-197. References to more recent work in this area include: (b) Callaghan, O.; Lampard, C.; Kennedy, A. R.; Murphy, J. A. Tetrahedron Lett. 1999, 40, 161-164. (c) Dupont, C.; Guénard, D.; Tchertanov, L.; Thoret, S.; Guéritte, F. Bioorg. Med. Chem. 1999, 7, 2961-2969. (d) Kizil, M.; Patro, B.; Callaghan, O.; Murphy, J. A.; Hursthouse, M. B.; Hibbs, D. J. Org. Chem. 1999, 64, 7856-7862. (e) Quinn, J. F.; Bos, M. E.; Wulff, W. D. Org. Lett. 1999, 1, 161-164. (f) Urrutia, A.; Rodriguez, G. Tetrahedron Lett. 1998, 39, 4143-4146. (g) Urrutia, A.; Rodriguez, J. G. Tetrahedron 1999, 55, 11095-11108. (h) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1998, 120, 13523-13524.
    • (1999) Bioorg. Med. Chem. , vol.7 , pp. 2961-2969
    • Dupont, C.1    Guénard, D.2    Tchertanov, L.3    Thoret, S.4    Guéritte, F.5
  • 11
    • 0032695066 scopus 로고    scopus 로고
    • For a recent review, see: (a) Saxton, J. E. In The Alkaloids', Cordell, G. A., Ed.; Academic: New York, 1998; Vol. 51, pp 1-197. References to more recent work in this area include: (b) Callaghan, O.; Lampard, C.; Kennedy, A. R.; Murphy, J. A. Tetrahedron Lett. 1999, 40, 161-164. (c) Dupont, C.; Guénard, D.; Tchertanov, L.; Thoret, S.; Guéritte, F. Bioorg. Med. Chem. 1999, 7, 2961-2969. (d) Kizil, M.; Patro, B.; Callaghan, O.; Murphy, J. A.; Hursthouse, M. B.; Hibbs, D. J. Org. Chem. 1999, 64, 7856-7862. (e) Quinn, J. F.; Bos, M. E.; Wulff, W. D. Org. Lett. 1999, 1, 161-164. (f) Urrutia, A.; Rodriguez, G. Tetrahedron Lett. 1998, 39, 4143-4146. (g) Urrutia, A.; Rodriguez, J. G. Tetrahedron 1999, 55, 11095-11108. (h) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1998, 120, 13523-13524.
    • (1999) J. Org. Chem. , vol.64 , pp. 7856-7862
    • Kizil, M.1    Patro, B.2    Callaghan, O.3    Murphy, J.A.4    Hursthouse, M.B.5    Hibbs, D.6
  • 12
    • 0033564997 scopus 로고    scopus 로고
    • For a recent review, see: (a) Saxton, J. E. In The Alkaloids', Cordell, G. A., Ed.; Academic: New York, 1998; Vol. 51, pp 1-197. References to more recent work in this area include: (b) Callaghan, O.; Lampard, C.; Kennedy, A. R.; Murphy, J. A. Tetrahedron Lett. 1999, 40, 161-164. (c) Dupont, C.; Guénard, D.; Tchertanov, L.; Thoret, S.; Guéritte, F. Bioorg. Med. Chem. 1999, 7, 2961-2969. (d) Kizil, M.; Patro, B.; Callaghan, O.; Murphy, J. A.; Hursthouse, M. B.; Hibbs, D. J. Org. Chem. 1999, 64, 7856-7862. (e) Quinn, J. F.; Bos, M. E.; Wulff, W. D. Org. Lett. 1999, 1, 161-164. (f) Urrutia, A.; Rodriguez, G. Tetrahedron Lett. 1998, 39, 4143-4146. (g) Urrutia, A.; Rodriguez, J. G. Tetrahedron 1999, 55, 11095-11108. (h) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1998, 120, 13523-13524.
    • (1999) Org. Lett. , vol.1 , pp. 161-164
    • Quinn, J.F.1    Bos, M.E.2    Wulff, W.D.3
  • 13
    • 0032482548 scopus 로고    scopus 로고
    • For a recent review, see: (a) Saxton, J. E. In The Alkaloids', Cordell, G. A., Ed.; Academic: New York, 1998; Vol. 51, pp 1-197. References to more recent work in this area include: (b) Callaghan, O.; Lampard, C.; Kennedy, A. R.; Murphy, J. A. Tetrahedron Lett. 1999, 40, 161-164. (c) Dupont, C.; Guénard, D.; Tchertanov, L.; Thoret, S.; Guéritte, F. Bioorg. Med. Chem. 1999, 7, 2961-2969. (d) Kizil, M.; Patro, B.; Callaghan, O.; Murphy, J. A.; Hursthouse, M. B.; Hibbs, D. J. Org. Chem. 1999, 64, 7856-7862. (e) Quinn, J. F.; Bos, M. E.; Wulff, W. D. Org. Lett. 1999, 1, 161-164. (f) Urrutia, A.; Rodriguez, G. Tetrahedron Lett. 1998, 39, 4143-4146. (g) Urrutia, A.; Rodriguez, J. G. Tetrahedron 1999, 55, 11095-11108. (h) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1998, 120, 13523-13524.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4143-4146
    • Urrutia, A.1    Rodriguez, G.2
  • 14
    • 0033520255 scopus 로고    scopus 로고
    • For a recent review, see: (a) Saxton, J. E. In The Alkaloids', Cordell, G. A., Ed.; Academic: New York, 1998; Vol. 51, pp 1-197. References to more recent work in this area include: (b) Callaghan, O.; Lampard, C.; Kennedy, A. R.; Murphy, J. A. Tetrahedron Lett. 1999, 40, 161-164. (c) Dupont, C.; Guénard, D.; Tchertanov, L.; Thoret, S.; Guéritte, F. Bioorg. Med. Chem. 1999, 7, 2961-2969. (d) Kizil, M.; Patro, B.; Callaghan, O.; Murphy, J. A.; Hursthouse, M. B.; Hibbs, D. J. Org. Chem. 1999, 64, 7856-7862. (e) Quinn, J. F.; Bos, M. E.; Wulff, W. D. Org. Lett. 1999, 1, 161-164. (f) Urrutia, A.; Rodriguez, G. Tetrahedron Lett. 1998, 39, 4143-4146. (g) Urrutia, A.; Rodriguez, J. G. Tetrahedron 1999, 55, 11095-11108. (h) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1998, 120, 13523-13524.
    • (1999) Tetrahedron , vol.55 , pp. 11095-11108
    • Urrutia, A.1    Rodriguez, J.G.2
  • 15
    • 0032583442 scopus 로고    scopus 로고
    • For a recent review, see: (a) Saxton, J. E. In The Alkaloids', Cordell, G. A., Ed.; Academic: New York, 1998; Vol. 51, pp 1-197. References to more recent work in this area include: (b) Callaghan, O.; Lampard, C.; Kennedy, A. R.; Murphy, J. A. Tetrahedron Lett. 1999, 40, 161-164. (c) Dupont, C.; Guénard, D.; Tchertanov, L.; Thoret, S.; Guéritte, F. Bioorg. Med. Chem. 1999, 7, 2961-2969. (d) Kizil, M.; Patro, B.; Callaghan, O.; Murphy, J. A.; Hursthouse, M. B.; Hibbs, D. J. Org. Chem. 1999, 64, 7856-7862. (e) Quinn, J. F.; Bos, M. E.; Wulff, W. D. Org. Lett. 1999, 1, 161-164. (f) Urrutia, A.; Rodriguez, G. Tetrahedron Lett. 1998, 39, 4143-4146. (g) Urrutia, A.; Rodriguez, J. G. Tetrahedron 1999, 55, 11095-11108. (h) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1998, 120, 13523-13524.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 13523-13524
    • Kozmin, S.A.1    Rawal, V.H.2
  • 16
  • 25
    • 0025021186 scopus 로고
    • Asymmetric total syntheses of aspidospermidine: (a) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521. (b) Desmaële, D.; d'Angelo, J. J. Org. Chem. 1994, 59, 2292-2303. (c) Schultz, A. G.; Pettus, L. J. Org. Chem. 1997, 62, 6855-6861. In addition, an asymmetric approach to the Stork tricyclic intermediate 2 has been reported: (d) Meyers, A. I.; Berney, D. J. Org. Chem. 1989, 54, 4673-4676.
    • (1990) J. Org. Chem. , vol.55 , pp. 517-521
    • Node, M.1    Nagasawa, H.2    Fuji, K.3
  • 26
    • 0028359968 scopus 로고
    • Asymmetric total syntheses of aspidospermidine: (a) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521. (b) Desmaële, D.; d'Angelo, J. J. Org. Chem. 1994, 59, 2292-2303. (c) Schultz, A. G.; Pettus, L. J. Org. Chem. 1997, 62, 6855-6861. In addition, an asymmetric approach to the Stork tricyclic intermediate 2 has been reported: (d) Meyers, A. I.; Berney, D. J. Org. Chem. 1989, 54, 4673-4676.
    • (1994) J. Org. Chem. , vol.59 , pp. 2292-2303
    • Desmaële, D.1    D'Angelo, J.2
  • 27
    • 0030873573 scopus 로고    scopus 로고
    • Asymmetric total syntheses of aspidospermidine: (a) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521. (b) Desmaële, D.; d'Angelo, J. J. Org. Chem. 1994, 59, 2292-2303. (c) Schultz, A. G.; Pettus, L. J. Org. Chem. 1997, 62, 6855-6861. In addition, an asymmetric approach to the Stork tricyclic intermediate 2 has been reported: (d) Meyers, A. I.; Berney, D. J. Org. Chem. 1989, 54, 4673-4676.
    • (1997) J. Org. Chem. , vol.62 , pp. 6855-6861
    • Schultz, A.G.1    Pettus, L.2
  • 28
    • 0024456198 scopus 로고
    • Asymmetric total syntheses of aspidospermidine: (a) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521. (b) Desmaële, D.; d'Angelo, J. J. Org. Chem. 1994, 59, 2292-2303. (c) Schultz, A. G.; Pettus, L. J. Org. Chem. 1997, 62, 6855-6861. In addition, an asymmetric approach to the Stork tricyclic intermediate 2 has been reported: (d) Meyers, A. I.; Berney, D. J. Org. Chem. 1989, 54, 4673-4676.
    • (1989) J. Org. Chem. , vol.54 , pp. 4673-4676
    • Meyers, A.I.1    Berney, D.2
  • 31
    • 0442282644 scopus 로고    scopus 로고
    • note
    • Synthesized from 1,4-butanediol by monobenzylation, PCC oxidation, vinyl Grignard addition, and Jones oxidation.
  • 32
    • 0442282646 scopus 로고    scopus 로고
    • note
    • For example, attempted azidation of the intermediate shown below resulted in cyclopropane formation as the major product. In addition, it did not prove feasible to open this cyclopropane with azide in a subsequent step. (Matrix Presented)


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