Construction of an Angular Tricyclic Benzofuran Skeleton Using the C-H Activation Strategy

Sun Q 1 , Guo F 2 , Liu Y 2 , Zhang Y 2 , Zhang K 2 , Wang Y 2 Show all authors , Gao Q 2 , Lim V 3 , Duan Y 2 , Fang L 1

Affiliations 

  • 1 Department of Pharmacy, The First Affiliated Hospital of Xinxiang Medical University, Xinxiang, Henan 453003, China
  • 2 School of Pharmacy, Xinxiang Medical University, 601 East Jinsui Avenue, Xinxiang, Henan 453003, P. R. China
  • 3 Advanced Medical and Dental Institute, Universiti Sains Malaysia, Bertam, Kepala Batas, Penang 13200, Malaysia
J Org Chem, 2024 Mar 01;89(5):3304-3308.
PMID: 38356371 DOI: 10.1021/acs.joc.3c02754

Abstract

A protocol for the construction of an angular tricyclic benzofuran skeleton based on the C-H activation strategy has been established. Different phthalide lactones on this skeleton can be easily assembled with various side chains by using C-H activation with aldehydes and subsequent reduction. This skeleton provides a versatile and crucial motif for the total synthesis of naturally occurring angular tricyclic benzofurans and their derivatives. Based on this protocol, the improved total syntheses of daldinin A and annullatin D were achieved in yields of 17.3 and 7.6%, respectively.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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