Biomimetic Synthesis of Complex Flavonoids Isolated from Daemonorops "Dragon's Blood"

Angew Chem Int Ed Engl. 2017 Sep 25;56(40):12332-12335. doi: 10.1002/anie.201705390. Epub 2017 Aug 16.

Abstract

The dragonbloodins are a pair of complex flavonoid trimers that have been isolated from the palm tree Daemonorops draco, one of the sources of the ancient resin known as "dragon's blood". We present a short synthesis that clarifies their relative configurations and sheds light on their origin in Nature. This synthesis features biomimetic cascade reactions that involve both ionic and radical intermediates. The biogenetic relationships between dracorhodin, the dracoflavans C, and the dragonbloodins A1 and A2 are discussed.

Keywords: autoxidation; biomimetic synthesis; cascade reactions; natural products; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arecaceae / chemistry*
  • Biomimetics*
  • Croton / chemistry*
  • Flavonoids / biosynthesis*
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Molecular Structure
  • Oxidation-Reduction
  • Plant Extracts / chemistry*
  • Resins, Plant / chemistry
  • Stereoisomerism

Substances

  • Flavonoids
  • Plant Extracts
  • Resins, Plant
  • dragon's blood