4.4 Article

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

Journal

TETRAHEDRON LETTERS
Volume 61, Issue 15, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2020.151754

Keywords

Cascade reactions; Radical reactions; Benzofurans; Synthetic methods

Funding

  1. JSPS KAKENHI [18H025550]
  2. Naito Foundation

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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.

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