P-71 Pd(II) 触媒による Yessotoxin の合成研究

DOI

書誌事項

タイトル別名
  • P-71 Synthetic studies of Yessotoxin

抄録

Yessotoxin was the polycyclic ether implicated in diarrhetic shellfish poisoning. Many synthetic efforts attracted our interest of synthesis towards Yessotoxin. We have been studying the novel methods to synthetic studies of natural products by using Pd(II) catalyst. One of our trials to develop the new annulation methods was the Pd(II)-catalyzed cyclization methods to ether. Herein we described the way to JK-ring and CD-ring fragments of Yessotoxin by Pd(II)-catalyzed cyclization. At first, we examined the synthesis of the JK-ring fragment. According our model studies, we intended the preparation of the Z-allyl alcohol. The vinyl iodide (4) and the aldehyde (19) were coupled, followed with the acid treatment to afford the triol (21). The triol (21) was treated with PdCl2(PhCN)2 in THF to give the bicyclic adduct (22). The successive transformation gave the JK-ring fragment (24). The structure and stereochemistry of the JK-ring fragment (24) was determined by analysis of 1H-NMR. Next, we described the synthesis of CD-ring fragment (31). The triol (30) was treated with PdCl2(PhCN)2 in THF, followed with oxidation and reduction to give the CD-ring fragment (31) in 64% yield. The structure and stereochemistry of this CD-ring fragment (31) was determined by X-ray crystallography. In summary, we attained the synthesis of the JK-ring and CD-ring fragments of Yessotoxin by Pd(II)-catalyzed cyclization. We are going on the further synthesis of Yessotoxin.

収録刊行物

詳細情報 詳細情報について

  • CRID
    1390285697597645824
  • NII論文ID
    130007906352
  • DOI
    10.24496/tennenyuki.59.0_489
  • ISSN
    24331856
  • 本文言語コード
    ja
  • データソース種別
    • JaLC
    • CiNii Articles
  • 抄録ライセンスフラグ
    使用不可

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