Abstract
A four-step synthesis of the extracyclic, antimalarial indole natural product decursivine is described starting from commercial piperonyl bromide and serotonin (see scheme). A photoinitiated reaction cascade involving indole radical cation formation, rearrangement, radical recombination, rearomatization, elimination, and diastereoselective auto-acid-catalyzed closure of the dihydrofuran ring combine in a single step to conclude this remarkably efficient synthesis.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 4445-4446 |
| Number of pages | 2 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 50 |
| Issue number | 19 |
| DOIs | |
| State | Published - May 2 2011 |
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Keywords
- antimalarials
- indoles
- natural products
- photochemistry
- total synthesis
ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
Cite this
Mascal, M., Modes, K. V., & Durmus, A. (2011). Concise photochemical synthesis of the antimalarial indole alkaloid decursivine. Angewandte Chemie - International Edition, 50(19), 4445-4446. https://doi.org/10.1002/anie.201006423