Pinnatoxin A の全合成 Total Synthesis of Pinnatoxin A

この論文にアクセスする

この論文をさがす

著者

抄録

The first total synthesis of pinnatoxin A (1), a Ca<SUP>2+</SUP>-channel activator isolated in 1995 by Uemura and co-workers from the shellfish <I>Pinna muricata</I>, is reported. The synthetic plan was based on Uemura's biosynthetic proposal, and consists of an intramolecular Diels-Alder reaction for construction of the G-ring as well as the macrocycle, followed by imine formation to establish the 6, 7-spiro-ring system. During this investigation, factors controlling the stereochemistry of the BCD bis-spiroketal ring system were investigated, and the chemoselectivity and efficiency of the Ni (II) /Cr (II) -mediated coupling protocol were demonstrated. This synthesis has also established the absolute stereochemistry of natural pinnatoxin A as the antipode of structure 1.

収録刊行物

  • 有機合成化学協会誌

    有機合成化学協会誌 58(9), 877-886, 2000-09-01

    The Society of Synthetic Organic Chemistry, Japan

参考文献:  30件中 1-30件 を表示

  • <no title>

    UEMURA D.

    J.Am.Chem.Soc. 117, 1155, 1995

    被引用文献9件

  • <no title>

    CHUO T.

    Tetrahedron Lett. 37, 4023, 1996

    被引用文献1件

  • <no title>

    CHUO T.

    Tetrahedron Lett. 37, 4027, 1996

    被引用文献1件

  • <no title>

    OTOFUJI T.

    Food Saint. Res. 31, 76, 1981

    被引用文献1件

  • <no title>

    ZHENG S. Z.

    J. Mar. Drugs 33, 33, 1990

    被引用文献1件

  • <no title>

    KURAMOTO M.

    J. Synth. Org. Chem. JPN. 57, 105, 1999

    被引用文献2件

  • <no title>

    SEKI T.

    Tetrahedron Lett. 36, 7093, 1995

    被引用文献4件

  • <no title>

    STEWART M.

    Tetrahedron Lett. 38, 4899, 1997

    被引用文献1件

  • <no title>

    HU T.

    J.Chem.Soc.,Chem.Commun. 1995, 2159

    被引用文献2件

  • <no title>

    TORIGOE K.

    J.Am.Chem.Soc. 110, 7876, 1988

    被引用文献4件

  • <no title>

    HU T.

    J, Nat. Prod. 59, 1010, 1996

    被引用文献2件

  • <no title>

    SUGIMOTO T.

    Tetrahedron Lett 38, 7379, 1997

    被引用文献2件

  • <no title>

    ISHIHARA J.

    Synlett 1998, 603

    被引用文献1件

  • <no title>

    NODA T.

    Synlett 1998, 298

    被引用文献1件

  • <no title>

    ISHIWATA A.

    Synlett 1999, 692

    被引用文献1件

  • <no title>

    NITTA A.

    Synlett 1999, 695

    被引用文献2件

  • <no title>

    KOLB H. C.

    Chem. Rev. 94, 2483, 1994

    被引用文献22件

  • <no title>

    LOBINS H.

    Helv. Chim. Acta 59, 2100, 1976

    被引用文献1件

  • <no title>

    FURUTA K.

    Tetrahedron Lett. 27, 4507, 1986

    被引用文献2件

  • <no title>

    NEGISHI E.

    J. Org. Chem. 45, 2526, 1980

    被引用文献2件

  • <no title>

    JADHAV P. K.

    J. Org. Chem. 51, 432, 1986

    被引用文献6件

  • <no title>

    JIN H.

    J. Am. Chem. Soc. 108, 5644, 1986

    被引用文献6件

  • <no title>

    TAKAI K.

    J. Am. Chem. Soc. 108, 6048, 1986

    被引用文献8件

  • <no title>

    STAMOS D. P.

    Tetrahedron Lett. 38, 6355, 1997

    被引用文献1件

  • <no title>

    CHEN C.

    J. Org. Chem. 60, 5386, 1995

    被引用文献2件

  • <no title>

    HOFFMAN H. M. R.

    Angew. Chem., Int. Ed. Engl. 22, 795, 1983

    被引用文献1件

  • <no title>

    JUNG M. E.

    J. Am. Chem. Soc. 113, 7813, 1991

    被引用文献1件

  • <no title>

    SUGIMOTO T.

    Synlett 1999, 541

    被引用文献1件

  • <no title>

    MCCAULEY J. A.

    J. Am. Chem. Soc. 120, 7647, 1998

    被引用文献3件

  • The first practical method for asymmetric epoxidation

    KATSUKI T.

    J. Am. Chem. Soc. 102, 5974-5976, 1980

    DOI 被引用文献37件

各種コード

  • NII論文ID(NAID)
    10008821884
  • NII書誌ID(NCID)
    AN0024521X
  • 本文言語コード
    JPN
  • 資料種別
    REV
  • ISSN
    00379980
  • NDL 記事登録ID
    5474971
  • NDL 雑誌分類
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL 請求記号
    Z17-256
  • データ提供元
    CJP書誌  NDL  J-STAGE 
ページトップへ