Pd(II)を用いた触媒的Ferrier環化反応の開発とその生物活性物質合成への応用  [in Japanese] Development of Ferrier(II) Carbocyclization Catalyzed by Pd(II) and Its Application to the Synthesis of Bioactive Substances  [in Japanese]

Access this Article

Search this Article

Author(s)

Abstract

Highly ftinctionalized cyclohexanes are useful intermediates for the synthesis of natural products and their derivatives having 6-membered ring systems. Among the preparation of chiral substituted cyclohexanes, Hg (II) salts mediated conversion of aldohexoses into cyclohexanones [Ferrier (II) carbocyclization] has become one of the most efficient and intriguing process. This article summarizes our recent works concerning the development of the catalytic Ferrier (II) carbocyclization mediated by Pd (II) salts and the application of this reaction to the total syntheses : i) β-glucosidase inhibitor, cyclophellitol, ii) all diastereoisomers of inositol and D-<I>myo</I>-inositol phosphates. It should be emphasized that PdCl<SUB>2</SUB>-mediated transformation enabled us to prepare such expensive inositol derivatives efficiently.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(2), 120-128, 2000-02-01

    The Society of Synthetic Organic Chemistry, Japan

References:  75

  • <no title>

    BOLS M.

    Carbohydrate Building Blocks, 1996

    Cited by (3)

  • <no title>

    FERRIER R. J.

    Chem. Rev. 93, 2779, 1993

    Cited by (6)

  • <no title>

    千田憲孝

    有合化 53, 858, 1995

    Cited by (2)

  • <no title>

    IIMORI T.

    Tetrahedron Lett. 37, 649, 1996

    Cited by (2)

  • <no title>

    WONG Y. -H. H.

    J. Biol. Chem. 261, 11083, 1985

    Cited by (1)

  • <no title>

    MECHADO A. S.

    Carbohydr. Res. 135, 231, 1985

    Cited by (1)

  • <no title>

    CHIDA N.

    Bull. Chem. Soc. Jpn. 64, 2118, 1991

    Cited by (3)

  • <no title>

    ADAM S.

    Tetrahedron Lett. 29, 6589, 1988

    Cited by (2)

  • <no title>

    LASZLO P.

    J. Carbohydr. Chem. 11, 587, 1992

    Cited by (2)

  • <no title>

    TAKAHASHI H.

    Tetrahedron Lett. 39, 6939, 1998

    Cited by (2)

  • <no title>

    ATSUMI S.

    J. Antibiot. 43, 49, 1990

    Cited by (3)

  • <no title>

    ATSUMI S.

    J. Antibiot. 43, 1579, 1990

    Cited by (1)

  • <no title>

    SINNOTT M. L.

    Chem.Rev. 90, 1171, 1990

    Cited by (4)

  • <no title>

    JESPERSEN T. M.

    Angew. Chem. Int. Ed. Engl. 33, 1778, 1994

    Cited by (1)

  • <no title>

    KNAPP S.

    Tetrahedron Lett. 33, 1025, 1992

    Cited by (1)

  • <no title>

    SCHMIDT D. D.

    Naturwissenschaften 64, 536, 1977

    Cited by (1)

  • <no title>

    ITOH J.

    J. Antibiot. 34, 1424, 1981

    Cited by (1)

  • <no title>

    YOKOSE K.

    J. Antibiot. 36, 1157, 1983

    Cited by (1)

  • <no title>

    SAUNIER B.

    J. Biol. Chem. 257, 14155, 1982

    Cited by (2)

  • <no title>

    PAN Y. T.

    Biochemistry 22, 3975, 1983

    Cited by (2)

  • <no title>

    ATSUMI S.

    Cancer Research 53, 4896, 1993

    Cited by (1)

  • <no title>

    TATSUTA K.

    Carbohydr. Res. 222, 189, 1991

    Cited by (3)

  • <no title>

    TATSUTA K.

    Tetrahedron Lett. 31, 1171, 1990

    Cited by (5)

  • <no title>

    MORITZ V.

    Tetrahedron Lett. 33, 5243, 1992

    Cited by (3)

  • <no title>

    SCHLESSINGER R. H.

    J. Org. Chem. 60, 16, 1995

    Cited by (1)

  • <no title>

    MCDEVITT R. E.

    J. Org. Chem. 59, 3250, 1994

    Cited by (1)

  • <no title>

    SHING T. K. M.

    J. Chem. Soc. Chem. Commun. 1993, 995

    Cited by (1)

  • <no title>

    AKIYAMA T.

    Synlett 1991, 831

    Cited by (4)

  • <no title>

    ELIEL E. L.

    Conformational Analysis. 352, 1965

    Cited by (2)

  • <no title>

    PELTER A.

    Tetrahedron Lett. 26, 5097, 1985

    Cited by (1)

  • <no title>

    PELTER A.

    Tetrahedron 49, 2965, 1993

    Cited by (3)

  • <no title>

    MONT-CHAMP J. L.

    J. Org. Chem. 58, 7679, 1993

    Cited by (1)

  • <no title>

    TAKAHASHI H.

    Tetrahedron Lett. 39, 9703, 1998

    Cited by (3)

  • <no title>

    TAKAHASHI H.

    Tetrahedron Lett. 39, 9707, 1998

    Cited by (2)

  • <no title>

    ANGYAL S. J.

    Aust. J. Chem. 20, 2117, 1967

    Cited by (1)

  • <no title>

    SASAKI K.

    Plant Phvsiol. 81, 493, 1986

    Cited by (1)

  • <no title>

    MICHELL R. H.

    Biochim. Biophys. Acta 415, 81, 1975

    Cited by (3)

  • <no title>

    BERRIDGE M. J.

    Nature(London) 312, 315, 1984

    Cited by (1)

  • <no title>

    LEY S. V.

    Tetrahedron 46, 4995, 1990

    Cited by (1)

  • <no title>

    BENDER S. L.

    J. Am. Chem. Soc. 113, 9883, 1991

    Cited by (2)

  • <no title>

    LEY S. V.

    Pure. Appl. Chem. 62, 2031, 1990

    Cited by (1)

  • <no title>

    BRUZIK K. S.

    J. Am. Chem. Soc. 114, 6361, 1992

    Cited by (3)

  • <no title>

    WATANABE Y.

    J. Chem. Soc., Chem. Commun. 1991, 428

    Cited by (1)

  • <no title>

    LIU Y. -C.

    Tetrahedron Lett. 30, 1617, 1989

    Cited by (1)

  • <no title>

    OZAKI S.

    Tetrahedron Lett. 28, 4691, 1987

    Cited by (1)

  • <no title>

    REDDY K. M.

    Tetrahedron Lett. 38, 4951, 1997

    Cited by (1)

  • <no title>

    STEB H.

    Nature(London) 306, 67, 1983

    Cited by (1)

  • <no title>

    IRVINE R. F.

    Nature 328, 386, 1987

    Cited by (2)

  • <no title>

    IRVINE R. F.

    Biochem. J. 240, 917, 1986

    Cited by (1)

  • <no title>

    竹縄忠臣

    情報伝達研究の新しい展開, 1993

    Cited by (1)

  • <no title>

    KOWARSKI A. R.

    J. Org. Chem. 38, 117, 1973

    Cited by (1)

  • <no title>

    MANDEL M.

    J. Chem. Soc., Perkin Trans. 1993, 741

    Cited by (1)

  • <no title>

    BALCI M.

    Tetrahedron. 46, 3715, 1990

    Cited by (3)

  • <no title>

    ANGYAL S. J.

    Carbohydr. Res. 20, 97

    Cited by (1)

  • <no title>

    Sigma社カタログ

    Cited by (1)

  • <no title>

    YAMAGUCHI N.

    Tetrahedron 50, 4125, 1994

    Cited by (1)

  • <no title>

    BENDER S. L.

    J. Am. Chem. Soc. 113, 9883, 1991

    Cited by (2)

  • <no title>

    ESTEVEZ V. A.

    J. Am. Chem. Soc. 113, 9885, 1991

    Cited by (1)

  • <no title>

    EVANS D. A.

    J. Am. Chem. Soc. 110, 3560, 1988

    Cited by (11)

  • <no title>

    SATO K.

    Bull. Chem. Soc. Jpn. 70, 885, 1997

    Cited by (5)

  • <no title>

    TORISAWA Y.

    Chem.Lett. 1984, 1555

    Cited by (4)

  • <no title>

    ANGYAL S. J.

    Carbohydr. Res. 100, 43, 1982

    Cited by (1)

  • <no title>

    SASAKI K.

    Carbohydr. Res. 183, 1, 1988

    Cited by (1)

  • <no title>

    LINDON J. C.

    Biochem. J. 233, 275, 1986

    Cited by (1)

  • <no title>

    LINDON J. C.

    Biochem. J. 244, 591, 1987

    Cited by (1)

  • <no title>

    CERDAN S.

    J. Biol. Chem. 261, 14676, 1986

    Cited by (1)

  • <no title>

    FERRIER R. J.

    J. Chem. Soc., Perkin Trans. 1, 1455, 1979

    DOI  Cited by (2)

  • <no title>

    ITO H.

    J. Am. Chem. Soc. 115, 8835, 1993

    DOI  Cited by (6)

  • <no title>

    BLATTNER R.

    J. Chem. Soc., Perkin Trans 1, 2413, 1985

    DOI  Cited by (1)

  • <no title>

    SHING T K. M.

    J. Chem. Soc., Perkin Trans 1, 2017, 1994

    DOI  Cited by (1)

  • <no title>

    SEMERIA D.

    Synthesis, 710-713, 1983

    DOI  Cited by (2)

  • <no title>

    GEMAL A. L.

    J. Am. Chem. Soc. 103, 5454-5459, 1981

    DOI  Cited by (19)

  • <no title>

    BILLINGTON D. C.

    Chem. Soc. Rev. 18, 83, 1989

    DOI  Cited by (4)

  • <no title>

    ANGYAL S. J.

    Carbohydr. Res. 266, 143-146, 1995

    Cited by (2)

  • <no title>

    PFITZNER K. E.

    J. Am. Chem. Soc. 85, 3027, 1963

    DOI  Cited by (3)

Cited by:  1

Codes

  • NII Article ID (NAID)
    10008819058
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    Journal Article
  • ISSN
    00379980
  • NDL Article ID
    4987415
  • NDL Source Classification
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL Call No.
    Z17-256
  • Data Source
    CJP  CJPref  NDL  J-STAGE 
Page Top