Journal
NATURE CHEMISTRY
Volume 7, Issue 11, Pages 879-882Publisher
NATURE PORTFOLIO
DOI: 10.1038/NCHEM.2336
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Funding
- Deutsche Forschungsgemeinschaft [SFB 749]
- Center for Integrated Protein Science, Munich
- Verband der Chemischen Industrie
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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.
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