4.4 Article

An Inverse Electron-Demand Diels-Alder-Based Total Synthesis of Urolithin M7

Journal

SYNLETT
Volume -, Issue 15, Pages 2245-2247

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1261203

Keywords

inverse electron demand Diels-Alder; domino reaction; dibenzopyranone; urolithin M7

Funding

  1. National Science and Engineering Research Council (NSERC) of Canada

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Urolithin M7 was synthesized from 2-hydroxy-4-methoxybenzaldehyde in 8 steps and 48% overall yield. The key step was an inverse electron demand Diels-Alder (IEDDA) reaction between diene 10 and the enamine (7) derived from dimethoxyacetaldehyde and pyrrolidine, which generated the 6H-dibenzo[b,d] pyran-6-one skeleton.

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