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Type: Journal article
Title: Biomimetic synthesis of the non-canonical PPAP natural products yezo'otogirin C and hypermogin D, and studies towards the synthesis of norascyronone A
Author: Sassnink, S.A.
Phan, Q.D.
Lam, H.C.
Day, A.J.
Murray, L.A.M.
George, J.H.
Citation: Organic and Biomolecular Chemistry, 2022; 20(8):1759-1768
Publisher: Royal Society of Chemistry
Issue Date: 2022
ISSN: 1477-0520
Statement of
Stefania A. Sassnink, Quang D. Phan, Hiu C. Lam, Aaron J. Day, Lauren A.M. Murray and Jonathan H. George
Abstract: Oxidative degradation and rearrangement of polycyclic polyprenylated acylphloroglucinols (PPAPs) has created diverse families of unique natural products that are attractive targets for biomimetic synthesis. Herein, we report a racemic synthesis of hyperibrin A and its oxidative radical cyclization to give yezo'otogirin C, followed by epoxidation and House-Meinwald rearrangement to give hypermogin D. We also investigated the biomimetic synthesis of norascyronone A via a similar radical cyclization pathway, with unexpected results that give insight into its biosynthesis.
Rights: This journal is © The Royal Society of Chemistry 2022
DOI: 10.1039/d2ob00074a
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Appears in Collections:Chemistry publications

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