Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 47, Pages 15587-15591Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809703
Keywords
biomimetic synthesis; cytochalasans; Diels-Alder cycloaddition; high-pressure chemistry; total synthesis
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Funding
- Deutsche Forschungsgemeinschaft [SFB 749]
- Alexander von Humboldt Stiftung
- National Institutes of Health [1R01GM126228]
- Carl Friedrich von Siemens Stiftung
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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.
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