Biomimetic Syntheses of Analogs of Hongoquercin A and B by Late-Stage Derivatization
2020
Mies, Thomas | White, Andrew J. P. | Parsons, Philip J. | Barrett, Anthony G. M.
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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