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

Matthias Schmid; Dirk Trauner

doi:10.1002/anie.201705390

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

Matthias Schmid, Dirk Trauner

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English (US)
Pages (from-to)	12332-12335
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	40
DOIs	https://doi.org/10.1002/anie.201705390
State	Published - Sep 25 2017

Keywords

autoxidation
biomimetic synthesis
cascade reactions
natural products
total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201705390

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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",

author = "Matthias Schmid and Dirk Trauner",

note = "Funding Information: We thank the German Research Foundation (DFG, SFB749) and the Studienstiftung des deutschen Volkes (German Academic Scholarship Foundation) for financial support. We also thank Prof. Dr. Frank Glorius and his co-worker Mario Wiesenfeldt for support and collaboration regarding the asymmetric hydrogenation of chrysin derivatives. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Trauner, Dirk

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N2 - 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.

AB - 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.

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KW - biomimetic synthesis

KW - cascade reactions

KW - natural products

KW - total synthesis

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

Abstract

Keywords

ASJC Scopus subject areas

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