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Type: Journal article
Title: Intramolecular Tricarbonyl-Ene Reactions and α-Hydroxy-β-Diketone Rearrangements Inspired by the Biosynthesis of Polycyclic Polyprenylated Acylphloroglucinols
Other Titles: Intramolecular Tricarbonyl-Ene Reactions and alpha-Hydroxy-beta-Diketone Rearrangements Inspired by the Biosynthesis of Polycyclic Polyprenylated Acylphloroglucinols
Author: Zur Bonsen, A.B.
Peralta, R.A.
Fallon, T.
Huang, D.M.
George, J.H.
Citation: Angewandte Chemie International Edition, 2022; 61(34):e202203311-1-e202203311-11
Publisher: Wiley
Issue Date: 2022
ISSN: 1433-7851
Statement of
Andreas B. zur Bonsen, Ricardo A. Peralta, Thoma sFallon, David M. Huang, and Jonathan H. George
Abstract: Structurally unique natural products pose biosynthetic puzzles whose solution can inspire new chemical reactions. Herein, we propose a unified biosynthetic pathway towards some complex meroterpenoids—the hyperireflexolides, biyoulactones, hybeanones and hypermonones. This hypothesis led to the discovery of uncatalyzed, intramolecular carbonyl-ene reactions that are spontaneous at room temperature. We also developed an anionic cascade reaction featuring an α-hydroxy-β-diketone rearrangement and an intramolecular aldol reaction to access four distinct natural product scaffolds from a common intermediate.
Keywords: Biomimetic Synthesis; Carbonyl-Ene Reaction; Cascade Reactions; Natural Products; Rearrangement
Description: Version of record online: July 14, 2022
Rights: © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCHGmbH.This is an open access article under the terms of the Creative Commons Attribution License,which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
DOI: 10.1002/anie.202203311
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Appears in Collections:Chemistry publications

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