메뉴 건너뛰기




Volumn 119, Issue 27, 1997, Pages 6226-6241

Free radical cyclizations in alkaloid total synthesis: (±)-21- oxogelsemine and (±)-gelsemine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; FREE RADICAL;

EID: 0030742816     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970089h     Document Type: Article
Times cited : (89)

References (82)
  • 1
    • 77957076168 scopus 로고
    • Manske, R. H. F., Ed.; Academic Press: New York
    • For reviews of literature related to Gelsemium alkaloids, see: Liu, Z.-J.; Lu, R.-R. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1988; Vol. 33, pp 83-140. Saxon, J. E. Nat. Prod. Rep. 1992, 393.
    • (1988) The Alkaloids , vol.33 , pp. 83-140
    • Liu, Z.-J.1    Lu, R.-R.2
  • 2
    • 0003763679 scopus 로고
    • For reviews of literature related to Gelsemium alkaloids, see: Liu, Z.-J.; Lu, R.-R. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1988; Vol. 33, pp 83-140. Saxon, J. E. Nat. Prod. Rep. 1992, 393.
    • (1992) Nat. Prod. Rep. , pp. 393
    • Saxon, J.E.1
  • 3
    • 1842540870 scopus 로고
    • Manske, R. H. F., Ed.; Academic Press: New York
    • See: Saxton, J. E. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1965; Vol. 8, pp 93-117.
    • (1965) The Alkaloids , vol.8 , pp. 93-117
    • Saxton, J.E.1
  • 6
    • 0001856425 scopus 로고
    • Conroy, H.; Chakrabarti, J. K. Tetrahedron Lett. 1959, 6. For revisions of the NMR spectroscopic properties of gelsemine, see: Schun, Y.; Cordell, G. A. J. Nat. Prod. 1985, 48, 969.
    • (1959) Tetrahedron Lett. , pp. 6
    • Conroy, H.1    Chakrabarti, J.K.2
  • 7
    • 0022373216 scopus 로고
    • Conroy, H.; Chakrabarti, J. K. Tetrahedron Lett. 1959, 6. For revisions of the NMR spectroscopic properties of gelsemine, see: Schun, Y.; Cordell, G. A. J. Nat. Prod. 1985, 48, 969.
    • (1985) J. Nat. Prod. , vol.48 , pp. 969
    • Schun, Y.1    Cordell, G.A.2
  • 9
    • 16944364474 scopus 로고
    • For isolation and structure of 21-oxogelsemine, see: Nikiforov, A. J.; Latzel, J.; Varmuza, K.; Wichtl, M. Monatsh. Chem. 1974, 105, 1292. For spectroscopic characterization of 21-oxogelsemine, see: Schun, Y.; Cordell, G. A.; Garland, M. J. Nat. Prod. 1986, 49, 483.
    • (1974) Monatsh. Chem. , vol.105 , pp. 1292
    • Nikiforov, A.J.1    Latzel, J.2    Varmuza, K.3    Wichtl, M.4
  • 10
    • 0022461551 scopus 로고
    • For isolation and structure of 21-oxogelsemine, see: Nikiforov, A. J.; Latzel, J.; Varmuza, K.; Wichtl, M. Monatsh. Chem. 1974, 105, 1292. For spectroscopic characterization of 21-oxogelsemine, see: Schun, Y.; Cordell, G. A.; Garland, M. J. Nat. Prod. 1986, 49, 483.
    • (1986) J. Nat. Prod. , vol.49 , pp. 483
    • Schun, Y.1    Cordell, G.A.2    Garland, M.3
  • 13
    • 0001609116 scopus 로고
    • Autrey, R. L., Tahk, F. C. Tetrahedron 1967, 23, 901. Autrey, R. L.; Tahk, F. C. Tetrahedron 1968, 24, 3337.
    • (1967) Tetrahedron , vol.23 , pp. 901
    • Autrey, R.L.1    Tahk, F.C.2
  • 14
    • 0002185054 scopus 로고
    • Autrey, R. L., Tahk, F. C. Tetrahedron 1967, 23, 901. Autrey, R. L.; Tahk, F. C. Tetrahedron 1968, 24, 3337.
    • (1968) Tetrahedron , vol.24 , pp. 3337
    • Autrey, R.L.1    Tahk, F.C.2
  • 17
    • 0000120468 scopus 로고
    • Fleming, I.; Loreto, M. A.; Michael, J. P.; Wallace, I. H. M. Tetrahedron Lett. 1982, 23, 2053. Fleming, I.; Loreto, M. A.; Wallace, I. H. M.; Michael, J. P. J. Chem. Soc., Perkin Trans. 7 1986, 349. Clarke, C.; Fleming, I.; Fortunak, M. D.; Gallagher, P. T.; Honan, M. C.; Mann, A.; Nubling, C. O.; Raithby, P. R.; Wolff, J. J. Tetrahedron 1988, 44, 3931. Fleming, I.; Moses, R. C.; Tercel, M.; Ziv, J. J. Chem. Soc., Perkin Trans. 1 1991, 617.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 2053
    • Fleming, I.1    Loreto, M.A.2    Michael, J.P.3    Wallace, I.H.M.4
  • 18
    • 37049084020 scopus 로고
    • Fleming, I.; Loreto, M. A.; Michael, J. P.; Wallace, I. H. M. Tetrahedron Lett. 1982, 23, 2053. Fleming, I.; Loreto, M. A.; Wallace, I. H. M.; Michael, J. P. J. Chem. Soc., Perkin Trans. 7 1986, 349. Clarke, C.; Fleming, I.; Fortunak, M. D.; Gallagher, P. T.; Honan, M. C.; Mann, A.; Nubling, C. O.; Raithby, P. R.; Wolff, J. J. Tetrahedron 1988, 44, 3931. Fleming, I.; Moses, R. C.; Tercel, M.; Ziv, J. J. Chem. Soc., Perkin Trans. 1 1991, 617.
    • (1986) J. Chem. Soc., Perkin Trans. , vol.7 , pp. 349
    • Fleming, I.1    Loreto, M.A.2    Wallace, I.H.M.3    Michael, J.P.4
  • 19
    • 0001368775 scopus 로고
    • Fleming, I.; Loreto, M. A.; Michael, J. P.; Wallace, I. H. M. Tetrahedron Lett. 1982, 23, 2053. Fleming, I.; Loreto, M. A.; Wallace, I. H. M.; Michael, J. P. J. Chem. Soc., Perkin Trans. 7 1986, 349. Clarke, C.; Fleming, I.; Fortunak, M. D.; Gallagher, P. T.; Honan, M. C.; Mann, A.; Nubling, C. O.; Raithby, P. R.; Wolff, J. J. Tetrahedron 1988, 44, 3931. Fleming, I.; Moses, R. C.; Tercel, M.; Ziv, J. J. Chem. Soc., Perkin Trans. 1 1991, 617.
    • (1988) Tetrahedron , vol.44 , pp. 3931
    • Clarke, C.1    Fleming, I.2    Fortunak, M.D.3    Gallagher, P.T.4    Honan, M.C.5    Mann, A.6    Nubling, C.O.7    Raithby, P.R.8    Wolff, J.J.9
  • 20
    • 37049071843 scopus 로고
    • Fleming, I.; Loreto, M. A.; Michael, J. P.; Wallace, I. H. M. Tetrahedron Lett. 1982, 23, 2053. Fleming, I.; Loreto, M. A.; Wallace, I. H. M.; Michael, J. P. J. Chem. Soc., Perkin Trans. 7 1986, 349. Clarke, C.; Fleming, I.; Fortunak, M. D.; Gallagher, P. T.; Honan, M. C.; Mann, A.; Nubling, C. O.; Raithby, P. R.; Wolff, J. J. Tetrahedron 1988, 44, 3931. Fleming, I.; Moses, R. C.; Tercel, M.; Ziv, J. J. Chem. Soc., Perkin Trans. 1 1991, 617.
    • (1991) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 617
    • Fleming, I.1    Moses, R.C.2    Tercel, M.3    Ziv, J.4
  • 21
    • 0000327376 scopus 로고
    • Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4133. Madin, A.; Overman, L. E. Tetrahedron Lett. 1992, 33, 4859. Early, W. G.; Jacobsen, E. J.; Meier, G. P.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3781. Earley, W. G.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3785. Overman, L. E.; Sharp, M. J. J. Org. Chem. 1992, 57, 1035.
    • (1987) J. Org. Chem. , vol.52 , pp. 4133
    • Abelman, M.M.1    Oh, T.2    Overman, L.E.3
  • 22
    • 0026714767 scopus 로고
    • Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4133. Madin, A.; Overman, L. E. Tetrahedron Lett. 1992, 33, 4859. Early, W. G.; Jacobsen, E. J.; Meier, G. P.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3781. Earley, W. G.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3785. Overman, L. E.; Sharp, M. J. J. Org. Chem. 1992, 57, 1035.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 4859
    • Madin, A.1    Overman, L.E.2
  • 23
    • 0023791191 scopus 로고
    • Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4133. Madin, A.; Overman, L. E. Tetrahedron Lett. 1992, 33, 4859. Early, W. G.; Jacobsen, E. J.; Meier, G. P.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3781. Earley, W. G.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3785. Overman, L. E.; Sharp, M. J. J. Org. Chem. 1992, 57, 1035.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 3781
    • Early, W.G.1    Jacobsen, E.J.2    Meier, G.P.3    Oh, T.4    Overman, L.E.5
  • 24
    • 0023732619 scopus 로고
    • Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4133. Madin, A.; Overman, L. E. Tetrahedron Lett. 1992, 33, 4859. Early, W. G.; Jacobsen, E. J.; Meier, G. P.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3781. Earley, W. G.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3785. Overman, L. E.; Sharp, M. J. J. Org. Chem. 1992, 57, 1035.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 3785
    • Earley, W.G.1    Oh, T.2    Overman, L.E.3
  • 25
    • 0000905524 scopus 로고
    • Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4133. Madin, A.; Overman, L. E. Tetrahedron Lett. 1992, 33, 4859. Early, W. G.; Jacobsen, E. J.; Meier, G. P.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3781. Earley, W. G.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3785. Overman, L. E.; Sharp, M. J. J. Org. Chem. 1992, 57, 1035.
    • (1992) J. Org. Chem. , vol.57 , pp. 1035
    • Overman, L.E.1    Sharp, M.J.2
  • 28
    • 0009687276 scopus 로고
    • Hiemstra, H.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1988, 53, 3884. Newcombe, N. J.; Ya, F.; Vijn, R. J.; Hiemstra, H.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1994, 767.
    • (1988) J. Org. Chem. , vol.53 , pp. 3884
    • Hiemstra, H.1    Vijn, R.J.2    Speckamp, W.N.3
  • 35
    • 16944366270 scopus 로고    scopus 로고
    • note
    • Experimental details for the preparation and cyclization of sulfide 19 are provided in the Supporting Information.
  • 36
    • 16944363300 scopus 로고    scopus 로고
    • note
    • 24
  • 37
    • 16944365738 scopus 로고    scopus 로고
    • note
    • A comparison of solid state and solution conformational preferences of several compounds reported herein will be reported elsewhere.
  • 38
    • 16944364530 scopus 로고
    • Although 3-buten-1-ol is commercially available, we found it convenient to prepare it using a variation of the following procedure: House, H. O.; Liang, W. C.; Weeks, P. D. J. Org. Chem. 1974, 39, 3104.
    • (1974) J. Org. Chem. , vol.39 , pp. 3104
    • House, H.O.1    Liang, W.C.2    Weeks, P.D.3
  • 39
    • 16944367085 scopus 로고
    • Although N-methylmaleimide is commercially available, we found it convenient to prepare for large scale work: Piutti, A.; Giustiniani, E. Gazz. Chim. Ital. 1896, 26, 431. Cava, M. P.; Deana, A. A.; Muth, K.; Mitchell, M. J. Org. Synth. 1961, 41, 93.
    • (1896) Gazz. Chim. Ital. , vol.26 , pp. 431
    • Piutti, A.1    Giustiniani, E.2
  • 40
    • 0010447208 scopus 로고
    • Although N-methylmaleimide is commercially available, we found it convenient to prepare for large scale work: Piutti, A.; Giustiniani, E. Gazz. Chim. Ital. 1896, 26, 431. Cava, M. P.; Deana, A. A.; Muth, K.; Mitchell, M. J. Org. Synth. 1961, 41, 93.
    • (1961) J. Org. Synth. , vol.41 , pp. 93
    • Cava, M.P.1    Deana, A.A.2    Muth, K.3    Mitchell, M.4
  • 42
    • 0000941492 scopus 로고
    • Grieco, P. A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1975, 30, 3760. Sharpless, B. K.; Young, M. W. J. Org. Chem. 1975, 40, 947.
    • (1975) J. Org. Chem. , vol.40 , pp. 947
    • Sharpless, B.K.1    Young, M.W.2
  • 43
    • 0343477293 scopus 로고
    • Hubert, J. C.; Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1975, 31, 1437. Chamberlin, A. R.; Chung, J. Y. L. Tetrahedron Lett. 1982, 23, 2619. Hart, D. J.; Yang, T.-K. J. Chem. Soc., Chem. Commun. 1983. 135.
    • (1975) Tetrahedron , vol.31 , pp. 1437
    • Hubert, J.C.1    Wijnberg, J.B.P.A.2    Speckamp, W.N.3
  • 44
    • 0000960281 scopus 로고
    • Hubert, J. C.; Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1975, 31, 1437. Chamberlin, A. R.; Chung, J. Y. L. Tetrahedron Lett. 1982, 23, 2619. Hart, D. J.; Yang, T.-K. J. Chem. Soc., Chem. Commun. 1983. 135.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 2619
    • Chamberlin, A.R.1    Chung, J.Y.L.2
  • 45
    • 37049100639 scopus 로고
    • Hubert, J. C.; Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1975, 31, 1437. Chamberlin, A. R.; Chung, J. Y. L. Tetrahedron Lett. 1982, 23, 2619. Hart, D. J.; Yang, T.-K. J. Chem. Soc., Chem. Commun. 1983. 135.
    • (1983) J. Chem. Soc., Chem. Commun. , pp. 135
    • Hart, D.J.1    Yang, T.-K.2
  • 49
    • 33947479967 scopus 로고
    • For the preparation of ethyl (triphenylphosphoranylidene)acetate, see: Denney, D. B.; Ross, S. T. J. Org. Chem. 1962, 27, 998.
    • (1962) J. Org. Chem. , vol.27 , pp. 998
    • Denney, D.B.1    Ross, S.T.2
  • 51
    • 16944365187 scopus 로고    scopus 로고
    • note
    • We thank Dr. Jeffrey Dener and Mr. Jonathan Dawson for performing these experiments.
  • 52
    • 84980115172 scopus 로고
    • Fischer, E.; Jourdan, F. Chem. Ber. 1883, 16, 2241. Sindwell, H. G.; van Orden, R. B. Chem. Rev. 1942, 30, 78.
    • (1883) Chem. Ber. , vol.16 , pp. 2241
    • Fischer, E.1    Jourdan, F.2
  • 57
    • 16944365976 scopus 로고
    • Joncs, K.; Thompson, M.; Wright, C. J. Chem. Soc., Chem. Commun. 1986, 115. Wright, C.; Shulkind, M.; Jones, K.; Thompson, M. Tetrahedron Lett. 1987, 28, 6389. Jones, K.; McCarthy, C. Tetrahedron Lett. 1989, 30, 2657.
    • (1986) J. Chem. Soc., Chem. Commun. , pp. 115
    • Joncs, K.1    Thompson, M.2    Wright, C.3
  • 58
    • 0023500155 scopus 로고
    • Joncs, K.; Thompson, M.; Wright, C. J. Chem. Soc., Chem. Commun. 1986, 115. Wright, C.; Shulkind, M.; Jones, K.; Thompson, M. Tetrahedron Lett. 1987, 28, 6389. Jones, K.; McCarthy, C. Tetrahedron Lett. 1989, 30, 2657.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6389
    • Wright, C.1    Shulkind, M.2    Jones, K.3    Thompson, M.4
  • 59
    • 0001027284 scopus 로고
    • Joncs, K.; Thompson, M.; Wright, C. J. Chem. Soc., Chem. Commun. 1986, 115. Wright, C.; Shulkind, M.; Jones, K.; Thompson, M. Tetrahedron Lett. 1987, 28, 6389. Jones, K.; McCarthy, C. Tetrahedron Lett. 1989, 30, 2657.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 2657
    • Jones, K.1    McCarthy, C.2
  • 62
    • 0001085108 scopus 로고
    • For a procedure for the preparation of 2-bromophenyl isocyanate using triphosgene, see: Eckert, H.; Forster, B. Angew. Chem. 1987, 99, 922.
    • (1987) Angew. Chem. , vol.99 , pp. 922
    • Eckert, H.1    Forster, B.2
  • 64
    • 0344039812 scopus 로고
    • Hendi, S. B.; Hendi, M. S.; Wolfe, J. F. Synth. Commun. 1987, 17, 13. Brown, C. A. J. Org. Chem. 1974, 39, 1324.
    • (1974) J. Org. Chem. , vol.39 , pp. 1324
    • Brown, C.A.1
  • 66
    • 16944366638 scopus 로고
    • Ph.D. Thesis, The Ohio State University
    • For model studies, see: Wu, S. C. Ph.D. Thesis, The Ohio State University, 1991.
    • (1991)
    • Wu, S.C.1
  • 69
    • 16944361945 scopus 로고    scopus 로고
    • note
    • 45
  • 71
    • 16944366729 scopus 로고
    • Ph.D. Thesis, University of Rochester
    • Landeryon, V. A. Ph.D. Thesis, University of Rochester, 1965; Diss. Abstr. 1965, 26, 2477.
    • (1965)
    • Landeryon, V.A.1
  • 72
    • 16944366854 scopus 로고
    • Landeryon, V. A. Ph.D. Thesis, University of Rochester, 1965; Diss. Abstr. 1965, 26, 2477.
    • (1965) Diss. Abstr. , vol.26 , pp. 2477
  • 74
    • 33644528891 scopus 로고
    • Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
    • (1983) J. Org. Chem. , vol.48 , pp. 4155
    • Dess, D.B.1    Martin, J.C.2
  • 75
    • 33751384984 scopus 로고
    • Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
    • (1993) J. Org. Chem. , vol.58 , pp. 2899
    • Ireland, R.E.1    Liu, L.2
  • 77
  • 79
    • 0028911641 scopus 로고
    • Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392. Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1995, 36, 2393.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2393
    • Petasis, N.A.1    Lu, S.-P.2
  • 80
    • 16944366002 scopus 로고    scopus 로고
    • note
    • We thank Professor G. Cordell for kindly supplying a sample of authentic 21-oxogelsemine.
  • 82
    • 2542447291 scopus 로고
    • For the preparation of (2-oxopropylidene) triphenylphosphorane, see: Ramirez, F.; Dershowitz, S. J. Org. Chem. 1957, 22, 41.
    • (1957) J. Org. Chem. , vol.22 , pp. 41
    • Ramirez, F.1    Dershowitz, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.