Synthetic study of perophoramidine: construction of pentacyclic core structure via SmI2-mediated reductive cyclization

• Ishida, Takayuki

• 竹本, 佳司

抄録

An intramolecular SmI2-mediated reductive cyclization of carbodiimides and unsaturated lactams was applied to functionalized substrates bearing tetrasubstituted olefins. The reaction afforded arylated spiro-2-iminoindolines in high yield. Although the stereochemistry of the product was different from the desired one, the optimized palladium-catalyzed aryl amidination realized the isomerization and C–N bond formation in a single step and resulted in efficient construction of pentacyclic core of perophoramidine synthetically equivalent to the Rainier's intermediate.

収録刊行物

• Tetrahedron

  Tetrahedron 69 (23), 4517-4523, 2013-06

  Elsevier Ltd.

キーワード

• Natural product
• Alkaloid
• Samarium diiodide
• Palladium catalysis
• Amidine

詳細情報

• CRID: 1050282810746491776
• NII論文ID: 120005244917
• NII書誌ID: AA00861787
• ISSN: 00404020
• DOI: 10.1016/j.tet.2013.04.039
• HANDLE: 2433/174063
• Web Site: https://api.elsevier.com/content/article/PII:S0040402013005772?httpAccept=text/xml
• Web Site: https://api.elsevier.com/content/article/PII:S0040402013005772?httpAccept=text/plain
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN