Total Synthesis of Naphterpin and Marinone Natural Products

  • Org Lett. 2019 Oct 18;21(20):8312-8315. doi: 10.1021/acs.orglett.9b03095.
Lauren A M Murray  1 ,  Thomas Fallon  1 ,  Christopher J Sumby  1 ,  Jonathan H George  1
Affiliations
  • 1. Department of Chemistry , University of Adelaide , Adelaide , South Australia 5005 , Australia.
PMID: 31549845 DOI: 10.1021/acs.orglett.9b03095
Abstract

A concise and divergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6π-electrocyclization, and two Diels-Alder reactions-which facilitated the first total synthesis of naphterpin itself in five steps from 2,5-dimethoxyphenol, alongside similar syntheses of 7-demethylnaphterpin and debromomarinone. Late-stage oxidation and bromination reactions were also investigated, leading to the first total syntheses of naphterpins B and C and isomarinone.

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