Abstract
The cytochalasans are a large family of polyketide natural products with potent bioactivities. Amongst them, the aspochalasins show particularly intricate and fascinating structures. To gain insight into their structural diversity and innate reactivity, we have developed a rapid synthesis of aspochalasin D, the central member of the family. It proceeded in 13 steps starting from divinyl carbinol and utilized a high pressure Diels–Alder reaction that features high regio- and stereoselectivity. So far, our work has culminated in a biomimetic synthesis of aspergillin PZ, an intricate pentacyclic aspochalasan.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 15587-15591 |
| Number of pages | 5 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 57 |
| Issue number | 47 |
| DOIs | |
| State | Published - Nov 19 2018 |
Keywords
- Diels–Alder cycloaddition
- biomimetic synthesis
- cytochalasans
- high-pressure chemistry
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
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Cite this
Reyes, J. R., Winter, N., Spessert, L., & Trauner, D. (2018). Biomimetic Synthesis of (+)-Aspergillin PZ. Angewandte Chemie - International Edition, 57(47), 15587-15591. https://doi.org/10.1002/anie.201809703