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Biomimetic syntheses of analogs of hongoquercin A and B by late-stage derivatization

Authors
  • Mies, T
  • White, AJP
  • Parsons, PJ
  • Barrett, AGM
Publication Date
Dec 01, 2020
Source
Spiral - Imperial College Digital Repository
Keywords
License
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Abstract

The hongoquercins are tetracyclic meroterpenoid natural products with the trans–transoid decalin-dihydrobenzopyran ring system, which display a range of different bioactivities. In this study, the syntheses of a range of hongoquercins using gold-catalyzed enyne cyclization reactions and further derivatization are described. The parent enyne resorcylate precursors were synthesized biomimetically from the corresponding dioxinone keto ester via regioselective acylation, Tsuji-Trost allylic decarboxylative rearrangement, and aromatization. The dioxinone keto ester 12 was prepared in 6 steps from geraniol using allylic functionalization and alkyne synthesis.

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