特異な構造や生物活性を有するテルペノイドの不斉全合成  [in Japanese] Asymmetric Total Synthesis of Terpenoids Possessing Novel Structure or Biological Activity  [in Japanese]

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Abstract

Asymmetric total synthesis of sarcophytols A and T, hippospongic acid A, octalactin A and glabrescol has been summarized in this review. Baker's yeast reduction is used as a chilarity induction method. Both enantiomers of sarcophytols A and T, an inhibitor of tumor promoter, were synthesized using stereospecific [2, 3] -Wittig rearrangement as the key step. The structure of hippospongic acid A exhibiting inhibitory activity for gastrulation of starfish embryos was revised by asymmetric synthesis and its absolute configuration was determined. A key compound for the synthesis of cytotoxic octalactin A was prepared efficiently starting from (-) -citronellol. A compound having the structure proposed for glabrescol, a meso-type triterpene containing five continuously linked tetrahydrofuran rings, and one of its diastereomer were synthesized enantioselectively. Comparison of NMR spectra of all of thus synthesized authentic diastereomers revealed that there was some mistakes in elucidation of the stereochemistry of the natural product.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(12), 1167-1177, 2000-12-01

    The Society of Synthetic Organic Chemistry, Japan

References:  69

  • <no title>

    KODAMA M.

    Tetrahedron Lett. 1975, 3065

    Cited by (4)

  • <no title>

    KODAMA M.

    Tetrahedron Lett. 1976, 1121

    Cited by (1)

  • <no title>

    KODAMA M.

    Tetrahedron Lett. 1977, 2763

    Cited by (1)

  • <no title>

    KODAMA M.

    Tetrahedron Lett. 1978, 3121

    Cited by (1)

  • <no title>

    SHIMADA K.

    Tetrahedron Lett. 22, 4275, 1981

    Cited by (1)

  • <no title>

    KODAMA M.

    Tetrahedron Lett. 23, 3397, 1982

    Cited by (3)

  • <no title>

    KODAMA M.

    Tetrahedron Lett. 25, 5781, 1984

    Cited by (1)

  • <no title>

    KODAMA M.

    Tetrahedron 44, 7055, 1988

    Cited by (2)

  • <no title>

    FUKUYAMA Y.

    Chem. Lett. 1992, 167

    Cited by (1)

  • <no title>

    KODAMA M.

    Chem. Lett. 1996, 809

    Cited by (1)

  • <no title>

    ESCHENMOSER W.

    Helv. Chim. Acta 66, 82, 1983

    Cited by (2)

  • <no title>

    CSUK R.

    Chem. Ber. 91, 49, 1991

    Cited by (1)

  • <no title>

    SIH C. J.

    Angew.Chem., Int.Ed.Engl. 23, 570, 1984

    Cited by (4)

  • <no title>

    森謙治

    有合化 41, 1044, 1983

    Cited by (2)

  • <no title>

    FUGANTI C.

    J. Org. Chem. 49, 4089, 1984

    Cited by (1)

  • <no title>

    KODAMA M.

    Tetrahedron Lett. 31, 4025, 1990

    Cited by (4)

  • <no title>

    KODAMA M.

    Tetrahedron Lett. 34, 8453, 1993

    Cited by (6)

  • <no title>

    KOBAYASHI M.

    Chem. Pharm. Bull. 27, 2382, 1979

    Cited by (3)

  • <no title>

    KOBAYASHI M.

    Chem. Pharm. Bull. 37, 2035, 1989

    Cited by (1)

  • <no title>

    KOBAYASHI M.

    Chem. Pharm. Bull. 37, 631, 1989

    Cited by (1)

  • <no title>

    KOBAYASHI M.

    J. Org. Chem. 55, 1947, 1990

    Cited by (1)

  • <no title>

    FUJIKI H.

    Cancer Surveys 2, 539, 1983

    Cited by (2)

  • <no title>

    FUJIKI H.

    J. Cancer Res. Clin. Oncol. 115, 25, 1989

    Cited by (2)

  • <no title>

    TAKAYANAGI H.

    J. Org. Chem. 59, 2700, 1994

    Cited by (3)

  • <no title>

    高柳久男

    有合化 53, 724, 1995

    Cited by (1)

  • <no title>

    TAKAHASHI T.

    J. Org. Chem. 57, 3521, 1992

    Cited by (3)

  • <no title>

    LI W. -DZ.

    Tetrahedron Lett. 40, 965, 1999

    Cited by (1)

  • <no title>

    SCHMIDT R. R.

    Angew. Chem., Int. Ed. Engl. 25, 212, 1986

    Cited by (23)

  • <no title>

    IVERSEN T.

    J. Chem. Soc., Chem. Commun. 1981, 1240

    Cited by (3)

  • <no title>

    FUKAZAWA Y.

    Tetrahedron Lett. 37, 1257, 1996

    Cited by (2)

  • <no title>

    TAKAHASHI T.

    Tetrahedron 43, 5499, 1987

    Cited by (9)

  • <no title>

    HOUK K. N.

    Science 231, 1108, 1986

    Cited by (12)

  • <no title>

    WU Y. -D.

    J. Org. Chem. 55, 1421, 1990

    Cited by (9)

  • <no title>

    KODAMA M.

    Tetrahedron Lett. 38, 4627, 1997

    Cited by (1)

  • <no title>

    TINTO W. F.

    Tetrahedron Lett. 34, 1705, 1993

    Cited by (1)

  • <no title>

    VIDARI G.

    Tetrahedron Lett. 34, 6485, 1993

    Cited by (3)

  • <no title>

    KODAMA M.

    Chem. Lett. 1997, 117

    Cited by (2)

  • <no title>

    MCWILLIAMS J. C.

    J. Am. Chem. Soc. 116, 8378, 1994

    Cited by (3)

  • <no title>

    BACH J.

    Tetrahedron Lett. 36, 3425, 1995

    Cited by (2)

  • <no title>

    BUSZEK K. R.

    Tetrahedron Lett. 36, 7189, 1995

    Cited by (3)

  • <no title>

    ANDRUS M. B.

    Tetrahedron Lett. 37, 5049, 1996

    Cited by (3)

  • <no title>

    HULME A. N.

    Tetrahedron Lett. 38, 8245, 1997

    Cited by (1)

  • <no title>

    INOUE S.

    Synlett 1998, 735

    Cited by (1)

  • <no title>

    HARRISON J. R.

    Synlett 1999, 972

    Cited by (1)

  • <no title>

    MATSUSHITA M.

    Chem. Lett. 1996, 1039

    Cited by (3)

  • <no title>

    SHARPLESS K. B.

    J. Org. Chem. 40, 947, 1975

    Cited by (5)

  • <no title>

    GRIECO P. A.

    J. Org. Chem. 41, 1485, 1976

    Cited by (7)

  • <no title>

    SHARPLESS K. B.

    J. Org. Chem. 57, 2768, 1992

    Cited by (18)

  • <no title>

    BECKER H.

    J. Org. Chem. 60, 3940, 1995

    Cited by (1)

  • <no title>

    STILL W. C.

    J. Am. Chem. Soc. 105, 2487, 1983

    Cited by (3)

  • <no title>

    HIOKI H.

    Synlett 1998, 729

    Cited by (1)

  • <no title>

    HIOKI H.

    Tetrahedron Lett. 39, 7745, 1998

    Cited by (1)

  • <no title>

    OHTA S.

    Tetrahedron Lett. 37, 2265, 1996

    Cited by (1)

  • <no title>

    YANAI M.

    Tetrahedron 54, 15609, 1998

    Cited by (1)

  • <no title>

    OHTA S.

    Tetrahedron Lett. 37, 7765, 1996

    Cited by (1)

  • <no title>

    TAKAGI R.

    Chem. Commun. 1997, 1887

    Cited by (2)

  • <no title>

    SNIDER B. B.

    Tetrahedron Lett. 38, 5453, 1997

    Cited by (1)

  • <no title>

    ZHENG Y. F.

    J. Org. Chem. 59, 5803, 1994

    Cited by (2)

  • <no title>

    TOKUMASU M.

    J. Chem. Soc., Perkin Trans. 1, 489, 1999

    Cited by (1)

  • <no title>

    TAKIKAWA H.

    J. Chem. Soc., Perkin Trans. 1999, 2271

    Cited by (1)

  • <no title>

    HARDING W. W.

    Tetrahedron Lett. 36, 9137, 1995

    Cited by (3)

  • <no title>

    WANG Z.-X.

    J. Am. Chem. Soc. 119, 11224, 1997

    Cited by (6)

  • <no title>

    NAGAWA I.

    Tetrahedron Lett. 1975, 1409

    Cited by (1)

  • <no title>

    XIONG Z.

    J. Am. Chem. Soc. 122, 4831, 2000

    Cited by (3)

  • <no title>

    SERVI S.

    Synthesis 1990, 1-25

    DOI  Cited by (12)

  • <no title>

    MILLER S. L.

    Tetrahedron 51, 11959, 1995

    DOI  Cited by (1)

  • <no title>

    TAPIOLAS D. M.

    J. Am. Chem. Soc. 113, 4682, 1991

    DOI  Cited by (6)

  • <no title>

    BUSZEK K. R.

    J. Am. Chem. Soc. 116, 5511, 1994

    DOI  Cited by (5)

  • <no title>

    BLUET G.

    Synlett 221, 2000

    DOI  Cited by (2)

Codes

  • NII Article ID (NAID)
    10008824516
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    ART
  • ISSN
    00379980
  • NDL Article ID
    5593981
  • 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  NDL  J-STAGE 
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