An eight-step synthesis of epicolactone reveals its biosynthetic origin

Pascal Ellerbrock, Nicolas Armanino, Marina K. Ilg, Robert Webster, Dirk Trauner

Research output: Contribution to journalArticlepeer-review

Abstract

Epicolactone is a recently isolated fungal metabolite that is highly complex for its size, and yet racemic. With its array of quaternary stereocentres, high degree of functionalization and intricate polycyclic structure, it poses a considerable challenge to synthesis, a challenge that can be met by understanding its biosynthetic origin. If drawn in a certain way, epicolactone reveals a pattern that resembles purpurogallin, the archetype of ubiquitous natural colourants formed via oxidative dimerization. Based on this insight, we designed a biomimetic synthesis of epicolactone that proceeds in only eight steps from vanillyl alcohol. We have isolated a key intermediate that supports our biosynthetic hypothesis and anticipate that an isomer of epicolactone stemming from our synthetic efforts could also be found as a natural product.

Original languageEnglish (US)
Pages (from-to)879-882
Number of pages4
JournalNature chemistry
Volume7
Issue number11
DOIs
StatePublished - Nov 1 2015

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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