Radical cascade cyclization for synthesizing 3,4-fused tricyclic benzofuran derivatives

Masaya Nakajima, Yusuke Kondo, Shun-ichi Nakano, Yusuke Adachi, Dongil Choi, Robert Franzen, Tetsuhiro Nemoto*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

Abstract

A new method for synthesizing 3,4-fused tricyclic 3-alkylidene dihydrobenzofuran derivatives was developed. Treatment of propargyl iodophenol derivatives with a tethered alkene at the three contiguous positions under the radical cascade reaction conditions induced the reaction of the generated vinyl radical intermediates with the internal alkene, producing tricyclic 3-alkylidene dihydrobenzofurans in 25%-93% yield. The reaction products could be utilized as the precursors for 3,4-fused tricyclic benzofurans. (C) 2020 Elsevier Ltd. All rights reserved.

Original languageEnglish
Article number151754
Number of pages4
JournalTetrahedron Letters
Volume61
Issue number15
DOIs
Publication statusPublished - 9 Apr 2020
MoE publication typeA1 Journal article-refereed

Keywords

  • Cascade reactions
  • Radical reactions
  • Benzofurans
  • Synthetic methods
  • DIPTOINDONESIN G
  • CARBOCYCLES
  • INSERTION
  • MALIBATOL

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