Abstract
A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.
| Original language | English |
|---|---|
| Pages (from-to) | 8609-8615 |
| Number of pages | 7 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 10 |
| Issue number | 43 |
| DOIs | |
| Publication status | Published - Nov 21 2012 |
| Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Moustafa, G. A. I., Kamada, Y., Tanaka, T., & Yoshimitsu, T. (2012). Stereoconvergent route to chiral cyclohexenone building blocks: Formal synthesis of (-)-dysidiolide. Organic and Biomolecular Chemistry, 10(43), 8609-8615. https://doi.org/10.1039/c2ob26532j