Diastereomeric Resolution of a Racemic Biarylboronic Acid and Its Application to Divergent Asymmetric Total Syntheses of Some Axially Chiral Natural Products

Chun Young Lee, Cheol-Hong Cheon

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The asymmetric total syntheses of deshydroxytetramethylcupressuflavone and desmethylkotanin and the synthesis of a key intermediate in the previous synthesis of hibarimicinone are described using an axially chiral biarylboronic acid, prepared by the diastereomeric resolution of the corresponding rac-boronic acid, as a common intermediate. Conversion of the boronic acid moiety into either a hydrogen atom or a hydroxy group by protodeboronation or oxidation enabled us to complete the total syntheses of deshydroxytetramethylcupressuflavone and desmethylkotanin and synthesis of a key intermediate in the previous total synthesis of hibarimicinone, respectively.

Original languageEnglish
Pages (from-to)549-554
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume358
Issue number4
DOIs
Publication statusPublished - 2016 Feb 18

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Biological Products
Acids
Boronic Acids
Hydrogen
Atoms
Oxidation

Keywords

  • axially chiral natural products
  • boronic acids
  • diastereomeric resolution
  • MIDA boronates
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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AB - The asymmetric total syntheses of deshydroxytetramethylcupressuflavone and desmethylkotanin and the synthesis of a key intermediate in the previous synthesis of hibarimicinone are described using an axially chiral biarylboronic acid, prepared by the diastereomeric resolution of the corresponding rac-boronic acid, as a common intermediate. Conversion of the boronic acid moiety into either a hydrogen atom or a hydroxy group by protodeboronation or oxidation enabled us to complete the total syntheses of deshydroxytetramethylcupressuflavone and desmethylkotanin and synthesis of a key intermediate in the previous total synthesis of hibarimicinone, respectively.

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