4.8 Article

Cascade Claisen and Meinwald Rearrangement for One-Pot Divergent Synthesis of Benzofurans and 2H-Chromenes

Journal

ORGANIC LETTERS
Volume 22, Issue 8, Pages 3004-3009

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00770

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Funding

  1. National Natural Science Foundation of China [NSFC 21502018]
  2. Fujian Agriculture and Forestry University Foundation for Distinguished Young Scholars [XJQ201623]
  3. Foundation of Key Laboratory of Biopesticide and Chemical Biology [Keylab2019-03]
  4. Guangdong Academic of Sciences Special Project of Science and Technology Development [2016GDASRC-0104]
  5. Research Grant Council of Hong Kong [GRF 16311716, 16303617, 16304618]

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A new cascade approach has been developed for the one-pot four-step divergent synthesis of polysubstituted benzofurans and 2H-chromenes, featuring a novel cascade aromatic Claisen rearrangement/Meinwald rearrangement/dehydrative or oxidative cyclization. This new method was demonstrated with 39 examples tolerating different substitutions at an epoxide, allylic ether, and aromatic ring, and we showcased its utility with the first total synthesis of natural product liparacid A in seven steps.

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