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 language | English (US) |
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Pages (from-to) | 879-882 |
Number of pages | 4 |
Journal | Nature chemistry |
Volume | 7 |
Issue number | 11 |
DOIs | |
State | Published - Nov 1 2015 |
ASJC Scopus subject areas
- General Chemistry
- General Chemical Engineering