An eight-step synthesis of epicolactone reveals its biosynthetic origin.

07:00 EST 1st November 2015 | BioPortfolio

Summary of "An eight-step synthesis of epicolactone reveals its biosynthetic origin."

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.


Journal Details

This article was published in the following journal.

Name: Nature chemistry
ISSN: 1755-4349
Pages: 879-882


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