Total Synthesis of the Neuroprotective Agent Cudraisoflavone J

Qili Lu, Dipesh S. Harmalkar, Guofeng Quan, Haeun Kwon, Jungsook Cho, Yongseok Choi, Dongho Lee, Kyeong Lee

Research output: Contribution to journalReview articlepeer-review

Abstract

Cudraisoflavone J (1), isolated fromCudrania tricuspidata, is a potent neuroprotective compound with a chiral center. Herein, we report the first total synthesis of racemic cudraisoflavone J (1) using a Claisen rearrangement and a Suzuki coupling reaction as the key steps. Racemic secondary alcohol was kinetically resolved to give (+)- and (−)-cudraisoflavone J with up to 97 and 88% enantiomeric excess, respectively. The modified Mosher’s method was used to elucidate the absolute configuration of naturally occurring cudraisoflavone J.

Original languageEnglish
Pages (from-to)1359-1365
Number of pages7
JournalJournal of Natural Products
Volume84
Issue number4
DOIs
Publication statusPublished - 2021 Apr 23

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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