Asymmetric methods for the synthesis of flavanones, chromanones, and azaflavanones

Antoinette E. Nibbs, Karl A Scheidt*

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

76 Scopus citations

Abstract

Flavanones, chromanones, and related structures are privileged natural products that display a wide variety of biological activities. Although flavanoids are abundant in nature, there are a limited number of available general and efficient synthetic methods for accessing molecules of this class in a stereoselective manner. Their structurally simple architectures belie the difficulties involved in installation and maintenance of the stereogenic configuration at the C2 position, which can be sensitive and can undergo epimerization under mildly acidic, basic, and thermal reaction conditions. This review presents the methods currently used to access these related structures. The synthetic methods include manipulation of the flavone/flavanone core, carbon-carbon bond formation, and carbon-heteroatom bond formation. Flavanoids are plant-derived natural products. Although they are ubiquitous in nature, general asymmetric methods for their generation are rarer, due to the lability of the stereochemistry at C2. We discuss methods for the generation of enantio-enriched flavanones, chromanones, andazaflavanones, including chemical and enzymatic resolution, asymmetric reduction, and conjugate addition reactions.

Original languageEnglish (US)
Pages (from-to)449-462
Number of pages14
JournalEuropean Journal of Organic Chemistry
Issue number3
DOIs
StatePublished - Jan 1 2012

Keywords

  • Asymmetric synthesis
  • Azaflavanones
  • Chromanones
  • Flavanones
  • Natural products
  • Total synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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