4.5 Article

Total Synthesis of the Natural Pyridocoumarins Goniothaline A and B

Journal

SYNTHESIS-STUTTGART
Volume 51, Issue 2, Pages 552-556

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610909

Keywords

total synthesis; goniothaline; Perkin reaction; silver-catalyzed cycloisomerization; selective demethylation

Funding

  1. National Research Foundation of Korea (NRF) - Ministry of Science, ICT & Future Planning [NRF-2017R1C1B1001826]

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In this paper, we report the first total synthesis of goniothaline A and B, which are rare natural pyridocoumarins isolated from Goniothalamus australis . The key feature of the synthesis of goniothaline A is high-yielding silver-catalyzed cycloisomerization to afford the pyridine moiety. In addition, goniothaline B, a natural 8-hydroxyquinoline derivative, is readily synthesized by the regioselective demethylation of goniothaline A.

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