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Volumn 118, Issue 26, 1996, Pages 6210-6219

The first asymmetric total syntheses of (+)-lycorine and (+)-1-deoxylycorine

Author keywords

[No Author keywords available]

Indexed keywords

LYCORINE;

EID: 0030037716     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9606440     Document Type: Article
Times cited : (81)

References (65)
  • 2
    • 77957083775 scopus 로고
    • Manske, R. H. F., Holmes, H. L., Eds; Academic Press: New York
    • Cook, J. W.; Loudon, J. D. In The Alkaloids; Manske, R. H. F., Holmes, H. L., Eds; Academic Press: New York, 1952; Vol. 2, p 331.
    • (1952) The Alkaloids , vol.2 , pp. 331
    • Cook, J.W.1    Loudon, J.D.2
  • 6
    • 0000427207 scopus 로고
    • For a review of the chemistry and biological effects of lycorine and related Amaryllidaceae alkaloids, see: Ghosal, S.; Saini, K. S.; Razdan, S. Phytochem. 1985, 24, 2141.
    • (1985) Phytochem. , vol.24 , pp. 2141
    • Ghosal, S.1    Saini, K.S.2    Razdan, S.3
  • 9
    • 77957033352 scopus 로고
    • Brossi, A., Ed.; Academic Press: New York
    • For recent reviews of the Amaryllidaceae alkaloids, see: (a) Martin, S. M. In The Alkaloids, Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 30, p 251. (b) Lewis, J. R. Nat. Prod. Rep. 1995, 12, 339.
    • (1987) The Alkaloids , vol.30 , pp. 251
    • Martin, S.M.1
  • 10
    • 0029132566 scopus 로고
    • For recent reviews of the Amaryllidaceae alkaloids, see: (a) Martin, S. M. In The Alkaloids, Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 30, p 251. (b) Lewis, J. R. Nat. Prod. Rep. 1995, 12, 339.
    • (1995) Nat. Prod. Rep. , vol.12 , pp. 339
    • Lewis, J.R.1
  • 12
    • 0000455605 scopus 로고
    • For prior consideration of the development of the C ring of lycorine by way of a Birch reduction. see: (a) Hendrickson, J. B.; Alder, R. W.; Dalton, D. R.; Hey, D. G. J. Org. Chem. 1969, 34, 2667. (b) Schultz, A. G. Acc. Chem. Res. 1990, 23, 207.
    • (1969) J. Org. Chem. , vol.34 , pp. 2667
    • Hendrickson, J.B.1    Alder, R.W.2    Dalton, D.R.3    Hey, D.G.4
  • 13
    • 0000908715 scopus 로고
    • For prior consideration of the development of the C ring of lycorine by way of a Birch reduction. see: (a) Hendrickson, J. B.; Alder, R. W.; Dalton, D. R.; Hey, D. G. J. Org. Chem. 1969, 34, 2667. (b) Schultz, A. G. Acc. Chem. Res. 1990, 23, 207.
    • (1990) Acc. Chem. Res. , vol.23 , pp. 207
    • Schultz, A.G.1
  • 16
    • 8944226491 scopus 로고    scopus 로고
    • note
    • (b) Benzamide 3 is prepared by procedures described in ref 12a or may be purchased from Aldrich Chemical Co. (34,836-8).
  • 17
    • 8944244900 scopus 로고    scopus 로고
    • For the genesis of this procedure, see ref 12a
    • For the genesis of this procedure, see ref 12a.
  • 21
    • 8944228836 scopus 로고    scopus 로고
    • Molecular modeling studies were carried out with MacroModel (MM2, Version 3.0)
    • Molecular modeling studies were carried out with MacroModel (MM2, Version 3.0).
  • 22
    • 8944222940 scopus 로고
    • For a more complete discussion of the facial, regio- and stereoselectivity of radical cyclizations of chiral enamides, see: Schultz, A. G.; Guzzo, P. R.; Nowak, D. M. J. Org. Chem. 1995, 60, 8040.
    • (1995) J. Org. Chem. , vol.60 , pp. 8040
    • Schultz, A.G.1    Guzzo, P.R.2    Nowak, D.M.3
  • 23
    • 8944221086 scopus 로고    scopus 로고
    • note
    • Enamide 11c also was prepared via acylation of 9 with piperonyloyl chloride to give 10c.
  • 25
    • 0001442190 scopus 로고
    • Brossi, A., Ed.; Academic Press: New York
    • (b) Ninomiya, I.; Naito, T. In The Alkaloids, Brossi, A., Ed.; Academic Press: New York, 1983; Vol. 22, p 189.
    • (1983) The Alkaloids , vol.22 , pp. 189
    • Ninomiya, I.1    Naito, T.2
  • 27
    • 37049092681 scopus 로고
    • For an alternative mechanism involving intermolecular hydrogen atom migration, see (a) Schultz, A. G.; Lucci, R. D. J. Chem. Soc., Chem. Commun. 1976, 925. (b) Schultz, A. G.; Lucci, R. D.; Fu, W. Y.; Berger, M. H.; Erhardt, J.; Hagmann, W. K. J. Am. Chem. Soc. 1978, 100, 2150.
    • (1976) J. Chem. Soc., Chem. Commun. , pp. 925
    • Schultz, A.G.1    Lucci, R.D.2
  • 34
    • 0011144448 scopus 로고
    • For earlier examples of radical-induced epoxide fragmentations, see: (a) Sabatino, E. C.; Gritter, R. J. J. Org. Chem. 1963, 28, 3437. (b) Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (e) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (f) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (g) Dang, H.-S.; Roberts, B. P. Tetrahedron Lett. 1992, 33, 6169.
    • (1963) J. Org. Chem. , vol.28 , pp. 3437
    • Sabatino, E.C.1    Gritter, R.J.2
  • 35
    • 37049097357 scopus 로고
    • For earlier examples of radical-induced epoxide fragmentations, see: (a) Sabatino, E. C.; Gritter, R. J. J. Org. Chem. 1963, 28, 3437. (b) Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (e) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (f) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (g) Dang, H.-S.; Roberts, B. P. Tetrahedron Lett. 1992, 33, 6169.
    • (1981) J. Chem. Soc., Perkin Trans. 1 , pp. 2363
    • Barton, D.H.R.1    Motherwell, R.S.H.2    Motherwell, W.B.3
  • 36
    • 0001185767 scopus 로고
    • For earlier examples of radical-induced epoxide fragmentations, see: (a) Sabatino, E. C.; Gritter, R. J. J. Org. Chem. 1963, 28, 3437. (b) Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (e) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (f) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (g) Dang, H.-S.; Roberts, B. P. Tetrahedron Lett. 1992, 33, 6169.
    • (1990) J. Org. Chem. , vol.55 , pp. 5181
    • Rawal, V.H.1    Newton, R.C.2    Krishnamurthy, V.3
  • 37
    • 0000570983 scopus 로고
    • For earlier examples of radical-induced epoxide fragmentations, see: (a) Sabatino, E. C.; Gritter, R. J. J. Org. Chem. 1963, 28, 3437. (b) Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (e) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (f) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (g) Dang, H.-S.; Roberts, B. P. Tetrahedron Lett. 1992, 33, 6169.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5106
    • Kim, S.1    Lee, S.2    Koh, J.S.3
  • 38
    • 0026750821 scopus 로고
    • For earlier examples of radical-induced epoxide fragmentations, see: (a) Sabatino, E. C.; Gritter, R. J. J. Org. Chem. 1963, 28, 3437. (b) Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (e) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (f) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (g) Dang, H.-S.; Roberts, B. P. Tetrahedron Lett. 1992, 33, 6169.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3439
    • Rawal, V.H.1    Krishnamurthy, V.2
  • 39
    • 0026739668 scopus 로고
    • For earlier examples of radical-induced epoxide fragmentations, see: (a) Sabatino, E. C.; Gritter, R. J. J. Org. Chem. 1963, 28, 3437. (b) Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (e) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (f) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (g) Dang, H.-S.; Roberts, B. P. Tetrahedron Lett. 1992, 33, 6169.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 4687
    • Rawal, V.H.1    Iwasa, S.2
  • 40
    • 0026785121 scopus 로고
    • For earlier examples of radical-induced epoxide fragmentations, see: (a) Sabatino, E. C.; Gritter, R. J. J. Org. Chem. 1963, 28, 3437. (b) Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (e) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (f) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (g) Dang, H.-S.; Roberts, B. P. Tetrahedron Lett. 1992, 33, 6169.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6169
    • Dang, H.-S.1    Roberts, B.P.2
  • 41
    • 0015973559 scopus 로고
    • For a nonstereoselective synthesis of racemic 22, see: Torssell, K. Tetrahedron Lett. 1974, 623.
    • (1974) Tetrahedron Lett. , pp. 623
    • Torssell, K.1
  • 47
    • 8944230568 scopus 로고
    • Ph.D. Thesis, Cornell University
    • Baker, J. A. Ph.D. Thesis, Cornell University, 1970.
    • (1970)
    • Baker, J.A.1
  • 48
    • 8944228834 scopus 로고
    • Ph.D. Thesis, Rensselaer Polytechnic Institute
    • Holoboski, M. A. Ph.D. Thesis, Rensselaer Polytechnic Institute, 1995.
    • (1995)
    • Holoboski, M.A.1
  • 50
    • 8944261285 scopus 로고    scopus 로고
    • 2 to the corresponding enone made the study of dienol silyl ether formation impractical; see ref 33
    • 2 to the corresponding enone made the study of dienol silyl ether formation impractical; see ref 33.
  • 52
  • 65
    • 8944222025 scopus 로고    scopus 로고
    • CA 55:3594c
    • CA 55:3594c.


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