Abstract
(Chemical Equation Presented) Designer elegance: The transannular aldol reaction of a cyclooctene diketone is the key step in this total synthesis of the natural enantiomer of merrilactone A (see scheme). The configuration of the two stereocenters generated in the formation of the central bicyclo[3.3.0]octane framework of the natural product was established using a specially designed bulky protecting group.
| Original language | English |
|---|---|
| Pages (from-to) | 4843-4848 |
| Number of pages | 6 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 45 |
| Issue number | 29 |
| DOIs | |
| Publication status | Published - 2006 Jul 17 |
| Externally published | Yes |
Keywords
- Aldol reaction
- Asymmetric synthesis
- Medium-ring compounds
- Protecting groups
- Terpenoids
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
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Cite this
Inoue, M., Sato, T., & Hirama, M. (2006). Asymmetric total synthesis of (-)-merrilactone A: Use of a bulky protecting group as long-range stereocontrolling element. Angewandte Chemie - International Edition, 45(29), 4843-4848. https://doi.org/10.1002/anie.200601358