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Volumn 18, Issue PART K, 1995, Pages 269-313

Total synthesis of bioactive natural spiroethers, tautomycin and oscillatoxin D

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EID: 77957081360     PISSN: 15725995     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1572-5995(96)80029-9     Document Type: Chapter
Times cited : (3)

References (167)
  • 26
    • 85119756719 scopus 로고
    • (a) Deslongchamps P. Stereoelectronic Effects in Organic Chemistry 1983 Pergamon Press New York 4 54
    • (1983) , pp. 4-54
    • Deslongchamps, P.1
  • 31
    • 0001077427 scopus 로고
    • (a) Transformations of spiroketal templates for remote chiral transfer to linear chain subunits in natural products synthesis, see Totah N.I. Schreiber S.L. J. Org. Chem. 56 1991 6255 6256
    • (1991) J. Org. Chem. , vol.56 , pp. 6255-6256
    • Totah, N.I.1    Schreiber, S.L.2
  • 45
    • 85119778144 scopus 로고    scopus 로고
    • The spiroketals 20 and 21 were prepared by the nucleophilic additions of Grignard reagent or dianion prepared by Cohen's procedure to the corresponding lactone, see ref. 19 .
  • 46
    • 85119738635 scopus 로고    scopus 로고
    • The preparation of spiroketals 22 and 23 were described in the following section.
  • 47
    • 85119758884 scopus 로고
    • Kirby A.J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen 1983 Springer-Verlag New York 209 221
    • (1983) , pp. 209-221
    • Kirby, A.J.1
  • 48
    • 85119762844 scopus 로고    scopus 로고
    • α epimer of 21 was detected on GC-analysis of recovered spiroketals. In the similar reaction at -78°C, however, no isomer of 21 was detected.
  • 49
    • 0000195079 scopus 로고
    • Hydoxy protecting group concerning non- and chelation of metal ions and Lewis acids, see: Chen X. Hortelano E.R. Eliel E.L. Frye S.V. and references cited therein J. Am. Chem. Soc. 112 1990 6130 6131
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6130-6131
    • Chen, X.1    Hortelano, E.R.2    Eliel, E.L.3    Frye, S.V.4
  • 62
  • 67
    • 85119773997 scopus 로고
    • Simpkins N.S. Sulphones in Organic Synthesis 1993 Pergamon Oxford
    • (1993)
    • Simpkins, N.S.1
  • 90
    • 85119776113 scopus 로고
    • Ubukata M. Cheng X.-C. Isono K. Symposium Papers of 33th Symposium on the Chemistry of Natural Products Osaka (Japan) 1991 643 650
    • (1991) , pp. 643-650
    • Ubukata, M.1    Cheng, X.-C.2    Isono, K.3
  • 94
    • 85119769714 scopus 로고    scopus 로고
    • Ueno, T.; Oikawa, M.; Oikawa, H.; Ichihara, A., unpublished results.
  • 95
    • 85119740626 scopus 로고    scopus 로고
    • Ueno, T.; Oikawa, M.; Oikawa, H.; Ichihara, A., unpublished results.
  • 96
    • 85119766245 scopus 로고
    • (a) Carruthers W. Cycloaddition Reactions in Organic Synthesis 1990 Pergamon Oxford
    • (1990)
    • Carruthers, W.1
  • 97
    • 85119765825 scopus 로고
    • (b) Curran D.P. The Cycloadditon Approach to b-Hydroxy Carbonyls 1990 Wiley
    • (1990)
    • Curran, D.P.1
  • 102
    • 85119763861 scopus 로고
    • Sargent M.V. Cresp T.M. E. Haslam Comprehensive Organic Chemistry Vol. 4 1979 Pergamon Oxford 693 744
    • (1979) , pp. 693-744
    • Sargent, M.V.1    Cresp, T.M.2
  • 110
    • 85119772951 scopus 로고    scopus 로고
    • Oikawa, H.; Ichihara, A., unpublished results.
  • 111
    • 85119739864 scopus 로고
    • Shibasaki group also reported highly enantioselective reduction of the compound related with 95 Nakamura S. Shimizu S. Nakada M. Shibasaki M. Symposium Papers of 36th Symposium on the Chemistry of Natural Products Hiroshima (Japan) 1994 611 618
    • (1994) , pp. 611-618
    • Nakamura, S.1    Shimizu, S.2    Nakada, M.3    Shibasaki, M.4
  • 143
    • 85119776766 scopus 로고
    • Abstract II Nakamura H. Park P. Kishi Y. 58th Annual Meeting of Chem. Soc. Jpn. Kyoto, Japan April 1989 1189
    • (1989) , pp. 1189
    • Nakamura, H.1    Park, P.2    Kishi, Y.3
  • 146
    • 85119732449 scopus 로고    scopus 로고
    • Moore, R. E., Personal communication, The antileukemic activity was based on an assay using a limited amount of oscillatoxin D.
  • 149
    • 27844466269 scopus 로고
    • (b) N-Methoxy-N-methylamide (Weinreb's amide) as acylating reagent Nahm S. Weinreb S.M. Tetrahedron Lett. 22 1981 3815 3818
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3815-3818
    • Nahm, S.1    Weinreb, S.M.2
  • 152
    • 85119723894 scopus 로고    scopus 로고
    • The desired diastereomer ( S configuration): δ (ppm) -0.021 and 0.017. The undesired diastereomer ( R configuration): δ (ppm) -0.006 and 0.025.
  • 160
    • 85119763768 scopus 로고
    • Perlmutter P. Conjugate Addition Reactions in Organic Chemistry 1992 Pergamon Press Oxford
    • (1992)
    • Perlmutter, P.1
  • 164
    • 85119754811 scopus 로고    scopus 로고
    • The natural form and the 7S-isomer were obtained slightly with the recovery of the starting 2 R , 4 S -isomer mainly and decompositions decreased their yields


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