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Volumn 61, Issue 2, 1996, Pages 573-580

Total synthesis of (-)-tetrahydropalmatine via chiral formamidine carbanions: Unexpected behavior with certain ortho-substituted electrophiles

Author keywords

[No Author keywords available]

Indexed keywords

CANADINE; TETRAHYDROPALMATINE;

EID: 0030047733     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951611q     Document Type: Article
Times cited : (84)

References (63)
  • 1
    • 0003818285 scopus 로고
    • Academic Press: New York
    • For reviews of isoquinoline alkaloids, see: (a) Shamma, M. The Isoquinoline Alkaloids: Chemistry and Pharmacology; Academic Press: New York, 1972. (b) Hanaoka, M. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: Orlando, FL 1988; Vol. 33, pp 141-230. (c) Beecher, C. W. W.; Kelleher, W. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley and Sons: New York, 1988; Vol. 6, pp 297-337. (d) Bhakuni, D. S.; Jain, S. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: Orlando, FL, 1986; Vol. 28, pp 95-181. (e) Shamma, M.; Moniot, J. L. Isoquinoline Alkaloids Research; Plenum Press: New York, 1978.
    • (1972) The Isoquinoline Alkaloids: Chemistry and Pharmacology
    • Shamma, M.1
  • 2
    • 77957061442 scopus 로고
    • Brossi, A., Ed.; Academic Press: Orlando, FL
    • For reviews of isoquinoline alkaloids, see: (a) Shamma, M. The Isoquinoline Alkaloids: Chemistry and Pharmacology; Academic Press: New York, 1972. (b) Hanaoka, M. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: Orlando, FL 1988; Vol. 33, pp 141-230. (c) Beecher, C. W. W.; Kelleher, W. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley and Sons: New York, 1988; Vol. 6, pp 297-337. (d) Bhakuni, D. S.; Jain, S. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: Orlando, FL, 1986; Vol. 28, pp 95-181. (e) Shamma, M.; Moniot, J. L. Isoquinoline Alkaloids Research; Plenum Press: New York, 1978.
    • (1988) The Alkaloids: Chemistry and Pharmacology , vol.33 , pp. 141-230
    • Hanaoka, M.1
  • 3
    • 0001610610 scopus 로고
    • Pelletier, S. W., Ed.; John Wiley and Sons: New York
    • For reviews of isoquinoline alkaloids, see: (a) Shamma, M. The Isoquinoline Alkaloids: Chemistry and Pharmacology; Academic Press: New York, 1972. (b) Hanaoka, M. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: Orlando, FL 1988; Vol. 33, pp 141-230. (c) Beecher, C. W. W.; Kelleher, W. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley and Sons: New York, 1988; Vol. 6, pp 297-337. (d) Bhakuni, D. S.; Jain, S. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: Orlando, FL, 1986; Vol. 28, pp 95-181. (e) Shamma, M.; Moniot, J. L. Isoquinoline Alkaloids Research; Plenum Press: New York, 1978.
    • (1988) Alkaloids: Chemical and Biological Perspectives , vol.6 , pp. 297-337
    • Beecher, C.W.W.1    Kelleher, W.J.2
  • 4
    • 0344628143 scopus 로고
    • Brossi, A., Ed.; Academic Press: Orlando, FL
    • For reviews of isoquinoline alkaloids, see: (a) Shamma, M. The Isoquinoline Alkaloids: Chemistry and Pharmacology; Academic Press: New York, 1972. (b) Hanaoka, M. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: Orlando, FL 1988; Vol. 33, pp 141-230. (c) Beecher, C. W. W.; Kelleher, W. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley and Sons: New York, 1988; Vol. 6, pp 297-337. (d) Bhakuni, D. S.; Jain, S. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: Orlando, FL, 1986; Vol. 28, pp 95-181. (e) Shamma, M.; Moniot, J. L. Isoquinoline Alkaloids Research; Plenum Press: New York, 1978.
    • (1986) The Alkaloids: Chemistry and Pharmacology , vol.28 , pp. 95-181
    • Bhakuni, D.S.1    Jain, S.2
  • 5
    • 0003450085 scopus 로고
    • Plenum Press: New York
    • For reviews of isoquinoline alkaloids, see: (a) Shamma, M. The Isoquinoline Alkaloids: Chemistry and Pharmacology; Academic Press: New York, 1972. (b) Hanaoka, M. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: Orlando, FL 1988; Vol. 33, pp 141-230. (c) Beecher, C. W. W.; Kelleher, W. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley and Sons: New York, 1988; Vol. 6, pp 297-337. (d) Bhakuni, D. S.; Jain, S. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: Orlando, FL, 1986; Vol. 28, pp 95-181. (e) Shamma, M.; Moniot, J. L. Isoquinoline Alkaloids Research; Plenum Press: New York, 1978.
    • (1978) Isoquinoline Alkaloids Research
    • Shamma, M.1    Moniot, J.L.2
  • 6
    • 84891785166 scopus 로고
    • ApSimon, J., Ed.; John Wiley and Sons: New York
    • (a) Kametani, T. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; John Wiley and Sons: New York, 1977; Vol. 3, pp 1-272.
    • (1977) The Total Synthesis of Natural Products , vol.3 , pp. 1-272
    • Kametani, T.1
  • 13
    • 0026563069 scopus 로고
    • For recent reviews, see: (a) Meyers, A. I. Tetrahedron 1992, 48, 2589. (b) Highsmith, T. K.; Meyers, A. I. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 1, pp 95-135.
    • (1992) Tetrahedron , vol.48 , pp. 2589
    • Meyers, A.I.1
  • 14
    • 0010528135 scopus 로고
    • Pearson, W., Ed.; JAI Press: Greenwich, CT
    • For recent reviews, see: (a) Meyers, A. I. Tetrahedron 1992, 48, 2589. (b) Highsmith, T. K.; Meyers, A. I. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 1, pp 95-135.
    • (1990) Advances in Heterocyclic Natural Product Synthesis , vol.1 , pp. 95-135
    • Highsmith, T.K.1    Meyers, A.I.2
  • 22
    • 0014452887 scopus 로고
    • For other approaches to the C(9)-C(10) D-ring substitution pattern in the protoberberine alkaloids, see: (a) Kametani, T.; Noguchi, L; Saito, K.; Kaneda, S. J. Chem. Soc. C 1969, 2036. (b) Narasimhan, N. S.; Mali, R. S.; Kulkarni, B. K. Tetrahedron 1983, 39, 1975. (c) Lenz, G. R. J. Org. Chem. 1974, 39, 2839. (d) Shono, T.; Hamaguehi, H.; Sasaki, M.; Fujita, S.; Nagami, K. J. Org. Chem. 1983, 48, 1621. (e) Kametani, T.; Iida, K.; Kikuchi, T.; Honda, T.; Ihara, M. J. Heterocycl. Chem, 1970, 7, 491. (f) Perkin, W. H.; Ray, J. N.; Robinson, R. J. Chem. Soc. 1925, 127, 740. (g) Battersby, A. R.; Southgate, R.; Staunton, J.; Hirst, M. J. Chem. Soc. C 1966, 1052. (h) Kiparissides, Z.; Fichtner, R. H.; Poplawski, J.; Nalliah, B. C.; MacLean, D. B. Can. J. Chem. 1980, 58, 2770.
    • (1969) J. Chem. Soc. C , pp. 2036
    • Kametani, T.1    Noguchi, L.2    Saito, K.3    Kaneda, S.4
  • 23
    • 0001235181 scopus 로고
    • For other approaches to the C(9)-C(10) D-ring substitution pattern in the protoberberine alkaloids, see: (a) Kametani, T.; Noguchi, L; Saito, K.; Kaneda, S. J. Chem. Soc. C 1969, 2036. (b) Narasimhan, N. S.; Mali, R. S.; Kulkarni, B. K. Tetrahedron 1983, 39, 1975. (c) Lenz, G. R. J. Org. Chem. 1974, 39, 2839. (d) Shono, T.; Hamaguehi, H.; Sasaki, M.; Fujita, S.; Nagami, K. J. Org. Chem. 1983, 48, 1621. (e) Kametani, T.; Iida, K.; Kikuchi, T.; Honda, T.; Ihara, M. J. Heterocycl. Chem, 1970, 7, 491. (f) Perkin, W. H.; Ray, J. N.; Robinson, R. J. Chem. Soc. 1925, 127, 740. (g) Battersby, A. R.; Southgate, R.; Staunton, J.; Hirst, M. J. Chem. Soc. C 1966, 1052. (h) Kiparissides, Z.; Fichtner, R. H.; Poplawski, J.; Nalliah, B. C.; MacLean, D. B. Can. J. Chem. 1980, 58, 2770.
    • (1983) Tetrahedron , vol.39 , pp. 1975
    • Narasimhan, N.S.1    Mali, R.S.2    Kulkarni, B.K.3
  • 24
    • 0011790087 scopus 로고
    • For other approaches to the C(9)-C(10) D-ring substitution pattern in the protoberberine alkaloids, see: (a) Kametani, T.; Noguchi, L; Saito, K.; Kaneda, S. J. Chem. Soc. C 1969, 2036. (b) Narasimhan, N. S.; Mali, R. S.; Kulkarni, B. K. Tetrahedron 1983, 39, 1975. (c) Lenz, G. R. J. Org. Chem. 1974, 39, 2839. (d) Shono, T.; Hamaguehi, H.; Sasaki, M.; Fujita, S.; Nagami, K. J. Org. Chem. 1983, 48, 1621. (e) Kametani, T.; Iida, K.; Kikuchi, T.; Honda, T.; Ihara, M. J. Heterocycl. Chem, 1970, 7, 491. (f) Perkin, W. H.; Ray, J. N.; Robinson, R. J. Chem. Soc. 1925, 127, 740. (g) Battersby, A. R.; Southgate, R.; Staunton, J.; Hirst, M. J. Chem. Soc. C 1966, 1052. (h) Kiparissides, Z.; Fichtner, R. H.; Poplawski, J.; Nalliah, B. C.; MacLean, D. B. Can. J. Chem. 1980, 58, 2770.
    • (1974) J. Org. Chem. , vol.39 , pp. 2839
    • Lenz, G.R.1
  • 25
    • 0000973521 scopus 로고
    • For other approaches to the C(9)-C(10) D-ring substitution pattern in the protoberberine alkaloids, see: (a) Kametani, T.; Noguchi, L; Saito, K.; Kaneda, S. J. Chem. Soc. C 1969, 2036. (b) Narasimhan, N. S.; Mali, R. S.; Kulkarni, B. K. Tetrahedron 1983, 39, 1975. (c) Lenz, G. R. J. Org. Chem. 1974, 39, 2839. (d) Shono, T.; Hamaguehi, H.; Sasaki, M.; Fujita, S.; Nagami, K. J. Org. Chem. 1983, 48, 1621. (e) Kametani, T.; Iida, K.; Kikuchi, T.; Honda, T.; Ihara, M. J. Heterocycl. Chem, 1970, 7, 491. (f) Perkin, W. H.; Ray, J. N.; Robinson, R. J. Chem. Soc. 1925, 127, 740. (g) Battersby, A. R.; Southgate, R.; Staunton, J.; Hirst, M. J. Chem. Soc. C 1966, 1052. (h) Kiparissides, Z.; Fichtner, R. H.; Poplawski, J.; Nalliah, B. C.; MacLean, D. B. Can. J. Chem. 1980, 58, 2770.
    • (1983) J. Org. Chem. , vol.48 , pp. 1621
    • Shono, T.1    Hamaguehi, H.2    Sasaki, M.3    Fujita, S.4    Nagami, K.5
  • 26
    • 84987337702 scopus 로고
    • For other approaches to the C(9)-C(10) D-ring substitution pattern in the protoberberine alkaloids, see: (a) Kametani, T.; Noguchi, L; Saito, K.; Kaneda, S. J. Chem. Soc. C 1969, 2036. (b) Narasimhan, N. S.; Mali, R. S.; Kulkarni, B. K. Tetrahedron 1983, 39, 1975. (c) Lenz, G. R. J. Org. Chem. 1974, 39, 2839. (d) Shono, T.; Hamaguehi, H.; Sasaki, M.; Fujita, S.; Nagami, K. J. Org. Chem. 1983, 48, 1621. (e) Kametani, T.; Iida, K.; Kikuchi, T.; Honda, T.; Ihara, M. J. Heterocycl. Chem, 1970, 7, 491. (f) Perkin, W. H.; Ray, J. N.; Robinson, R. J. Chem. Soc. 1925, 127, 740. (g) Battersby, A. R.; Southgate, R.; Staunton, J.; Hirst, M. J. Chem. Soc. C 1966, 1052. (h) Kiparissides, Z.; Fichtner, R. H.; Poplawski, J.; Nalliah, B. C.; MacLean, D. B. Can. J. Chem. 1980, 58, 2770.
    • (1970) J. Heterocycl. Chem , vol.7 , pp. 491
    • Kametani, T.1    Iida, K.2    Kikuchi, T.3    Honda, T.4    Ihara, M.5
  • 27
    • 0011822559 scopus 로고
    • For other approaches to the C(9)-C(10) D-ring substitution pattern in the protoberberine alkaloids, see: (a) Kametani, T.; Noguchi, L; Saito, K.; Kaneda, S. J. Chem. Soc. C 1969, 2036. (b) Narasimhan, N. S.; Mali, R. S.; Kulkarni, B. K. Tetrahedron 1983, 39, 1975. (c) Lenz, G. R. J. Org. Chem. 1974, 39, 2839. (d) Shono, T.; Hamaguehi, H.; Sasaki, M.; Fujita, S.; Nagami, K. J. Org. Chem. 1983, 48, 1621. (e) Kametani, T.; Iida, K.; Kikuchi, T.; Honda, T.; Ihara, M. J. Heterocycl. Chem, 1970, 7, 491. (f) Perkin, W. H.; Ray, J. N.; Robinson, R. J. Chem. Soc. 1925, 127, 740. (g) Battersby, A. R.; Southgate, R.; Staunton, J.; Hirst, M. J. Chem. Soc. C 1966, 1052. (h) Kiparissides, Z.; Fichtner, R. H.; Poplawski, J.; Nalliah, B. C.; MacLean, D. B. Can. J. Chem. 1980, 58, 2770.
    • (1925) J. Chem. Soc. , vol.127 , pp. 740
    • Perkin, W.H.1    Ray, J.N.2    Robinson, R.3
  • 28
    • 20544470663 scopus 로고
    • For other approaches to the C(9)-C(10) D-ring substitution pattern in the protoberberine alkaloids, see: (a) Kametani, T.; Noguchi, L; Saito, K.; Kaneda, S. J. Chem. Soc. C 1969, 2036. (b) Narasimhan, N. S.; Mali, R. S.; Kulkarni, B. K. Tetrahedron 1983, 39, 1975. (c) Lenz, G. R. J. Org. Chem. 1974, 39, 2839. (d) Shono, T.; Hamaguehi, H.; Sasaki, M.; Fujita, S.; Nagami, K. J. Org. Chem. 1983, 48, 1621. (e) Kametani, T.; Iida, K.; Kikuchi, T.; Honda, T.; Ihara, M. J. Heterocycl. Chem, 1970, 7, 491. (f) Perkin, W. H.; Ray, J. N.; Robinson, R. J. Chem. Soc. 1925, 127, 740. (g) Battersby, A. R.; Southgate, R.; Staunton, J.; Hirst, M. J. Chem. Soc. C 1966, 1052. (h) Kiparissides, Z.; Fichtner, R. H.; Poplawski, J.; Nalliah, B. C.; MacLean, D. B. Can. J. Chem. 1980, 58, 2770.
    • (1966) J. Chem. Soc. C , pp. 1052
    • Battersby, A.R.1    Southgate, R.2    Staunton, J.3    Hirst, M.4
  • 29
    • 0001565939 scopus 로고
    • For other approaches to the C(9)-C(10) D-ring substitution pattern in the protoberberine alkaloids, see: (a) Kametani, T.; Noguchi, L; Saito, K.; Kaneda, S. J. Chem. Soc. C 1969, 2036. (b) Narasimhan, N. S.; Mali, R. S.; Kulkarni, B. K. Tetrahedron 1983, 39, 1975. (c) Lenz, G. R. J. Org. Chem. 1974, 39, 2839. (d) Shono, T.; Hamaguehi, H.; Sasaki, M.; Fujita, S.; Nagami, K. J. Org. Chem. 1983, 48, 1621. (e) Kametani, T.; Iida, K.; Kikuchi, T.; Honda, T.; Ihara, M. J. Heterocycl. Chem, 1970, 7, 491. (f) Perkin, W. H.; Ray, J. N.; Robinson, R. J. Chem. Soc. 1925, 127, 740. (g) Battersby, A. R.; Southgate, R.; Staunton, J.; Hirst, M. J. Chem. Soc. C 1966, 1052. (h) Kiparissides, Z.; Fichtner, R. H.; Poplawski, J.; Nalliah, B. C.; MacLean, D. B. Can. J. Chem. 1980, 58, 2770.
    • (1980) Can. J. Chem. , vol.58 , pp. 2770
    • Kiparissides, Z.1    Fichtner, R.H.2    Poplawski, J.3    Nalliah, B.C.4    MacLean, D.B.5
  • 32
    • 0012860351 scopus 로고
    • Ph.D. thesis, Colorado State University
    • Preliminary work was carried out with achiral formamidines: Hellring, S. D. Ph.D. thesis, Colorado State University, 1982. See also: Edwards, P. D.; Meyers, A. I. Tetrahedron Lett. 1984, 25, 939.
    • (1982)
    • Hellring, S.D.1
  • 33
    • 0012860351 scopus 로고
    • Preliminary work was carried out with achiral formamidines: Hellring, S. D. Ph.D. thesis, Colorado State University, 1982. See also: Edwards, P. D.; Meyers, A. I. Tetrahedron Lett. 1984, 25, 939.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 939
    • Edwards, P.D.1    Meyers, A.I.2
  • 47
    • 13344275327 scopus 로고    scopus 로고
    • note
    • 4 has, without exception, exceeded 95% ee. However, in an early experiment (M. Bos in this laboratory), it was noted that a benzyl chloride containing an ο-carboethoxy substituent gave nearly racemic material when alkylating a chiral formamidme such as 18 (unpublished result, 1984).
  • 53
    • 13344260148 scopus 로고    scopus 로고
    • note
    • We thank Professor W. H. Pirkle at the University of Illinois Urbana-Champaign and Dr. Christopher J. Welch at Regis Technologies, Inc., for helpful discussions and the use of the β-GEM I semipreparative column described in this work.
  • 63
    • 13344282227 scopus 로고    scopus 로고
    • note
    • Electrophile and THF combined over 4 Åmolecular sieves at least 2 h prior to reaction.


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