4.8 Article

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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 40, Pages 12332-12335

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705390

Keywords

autoxidation; biomimetic synthesis; cascade reactions; natural products; total synthesis

Funding

  1. German Research Foundation (DFG) [SFB749]
  2. Studienstiftung des deutschen Volkes (German Academic Scholarship Foundation)

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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 dragonbloodinsA1 and A2 are discussed.

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