Biomimetic synthesis of the non-canonical PPAP natural products yezo'otogirin C and hypermogin D, and studies towards the synthesis of norascyronone A
Organic & Biomolecular Chemistry, 2022•pubs.rsc.org
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 …
(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 …
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.
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