Efficient Methods for Synthesis of Polycyclic Ethers and Their Application

• Nakata Tadashi

  Department of Chemistry, Faculty of Science, Tokyo University of Science

Bibliographic Information

Other Title

• 多環状エーテルの効率的合成法の開発と応用
• タカンジョウ エーテル ノ コウリツテキ ゴウセイホウ ノ カイハツ ト オウヨウ

Abstract

Marine polycyclic ethers exemplified by brevetoxin B, a red tide toxin, have a unique trans-fused polycyclic ether ring system. Their synthetically challenging complex structures and potent bioactivities have attracted the attention of numerous synthetic organic chemists. We have already developed several efficient methods for synthesis of cyclic ethers based on the SmI₂-induced reductive cyclization of β-alkoxyacrylate, β-alkoxyvinyl sulfone, and β-alkoxyvinyl sulfoxide with high stereoselectivity. Iterative and two-directional strategies for the construction of polycyclic ethers were developed based on the above methods. Several convergent strategies for the synthesis of polycyclic ethers were also developed based on acetylide-triflate coupling, acetylide-aldehyde coupling, or intramolecular Barbier reaction, respectively. Total syntheses of brevetoxin B, mucocin, and pyragonicin were accomplished as application of the developed methods.

Journal

• Journal of Synthetic Organic Chemistry, Japan

  Journal of Synthetic Organic Chemistry, Japan 66 (4), 344-357, 2008

  The Society of Synthetic Organic Chemistry, Japan

Keywords

• samarium diiodide, tetrahydropyran
• oxepane
• β-alkoxyacrylate
• β-alkoxyvinyl sulfone
• β-alkoxyvinyl sulfoxide
• cyclization
• convergent synthesis
• brevetoxin
• mucocin

Details

• CRID: 1390001205313094016
• NII Article ID: 10021174540
• NII Book ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.66.344
• ISSN: 18836526
• ISSN: 00379980
• NDL BIB ID: 9459985
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I9459985
• Text Lang: ja
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed