ポリ環状エーテル類の長大な連続縮環システムの収束合成

• 坂井 健男

  名城大学薬学部

書誌事項

タイトル別名

• Convergent Synthesis of Fused Ring Systems in Large Polycyclic Ethers
• ポリ カンジョウ エーテルルイ ノ チョウダイ ナ レンゾクシュクカン システム ノ シュウソク ゴウセイ

抄録

 This article reviews our studies on the oxiranyl anion-based, [X+2+Y]-type convergent strategy for the synthesis of polycyclic ether natural products. The strategy is noteworthy for its flexibility, which allows for the generation of different-sized fused ring systems based on a ring expansion reaction. For a precise understanding of this key ring expansion, we first focused on the reaction mechanism, in which an equatorial attack of TMS-diazomethane was determined to be the crucial step. In the later part of this review, the application of our oxiranyl anion-based strategy to large fused ring systems is described. The advantageous flexibility is highlighted in the divergent synthesis of five octacyclic ethers involving the CDEFGHIJ-ring skeleton of yessotoxin and its ring-modified analogs. Total synthesis of gymnocin-A was achieved using the oxiranyl anion convergent strategy, which furnished its large system of fourteen contiguous ether rings.<br>

収録刊行物

• 薬学雑誌

  薬学雑誌 137 (9), 1095-1101, 2017-09-01

  公益社団法人 日本薬学会

キーワード

• marine natural product
• polycyclic ether
• oxiranyl anion
• convergent synthesis
• ring expansion

詳細情報

• CRID: 1390282681194153216
• NII論文ID: 130006038242
• NII書誌ID: AN00284903
• DOI: 10.1248/yakushi.17-00116
• ISSN: 13475231
• ISSN: 00316903
• NDL書誌ID: 028513715
• PubMed: 28867696
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I028513715
• Web Site: https://www.jstage.jst.go.jp/article/yakushi/137/9/137_17-00116/_pdf
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• 抄録ライセンスフラグ: 使用不可