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Type: Journal article
Title: Bioinspired total synthesis of erectones A and B, and the revised structure of hyperelodione D
Author: Franov, L.J.
Hart, J.D.
Pullella, G.A.
Sumby, C.J.
George, J.H.
Citation: Angewandte Chemie International Edition, 2022; 61(19):e202200420-1-e202200420-5
Publisher: Wiley
Issue Date: 2022
ISSN: 1433-7851
Statement of
Liam J. Franov, Jacob D. Hart, Glenn A. Pullella, Christopher J. Sumby, and Jonathan H. George
Abstract: The field of biomimetic synthesis seeks to apply biosynthetic hypotheses to the efficient construction of complex natural products. This approach can also guide the revision of incorrectly assigned structures. Herein, we describe the evolution of a concise total synthesis and structural reassignment of hyperelodione D, a tetracyclic meroterpenoid derived from a Hypericum plant, alongside some biogenetically related natural products, erectones A and B. The key step in the synthesis of hyperelodione D forms six stereocentres and three rings in a bioinspired cascade reaction that features an intermolecular Diels-Alder reaction, an intramolecular Prins reaction and a terminating cycloetherification.
Keywords: Biomimetic synthesis; cascade reactions; Diels–Alder reactions; structure elucidation; total synthesis
Description: Version of record online: March 14, 2022
Rights: © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. 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.202200420
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Appears in Collections:Chemistry publications

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