| Autor: |
Clayden J; School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK. j.p.clayden@manchester.ac.uk, Knowles FE, Baldwin IR |
| Jazyk: |
angličtina |
| Zdroj: |
Journal of the American Chemical Society [J Am Chem Soc] 2005 Mar 02; Vol. 127 (8), pp. 2412-3. |
| DOI: |
10.1021/ja042415g |
| Abstrakt: |
The neuroactive algal metabolite (-)-isodomoic acid C, a kainoid amino acid, has been synthesized for the first time. Asymmetric dearomatizing cyclization of an aromatic amide using a chiral lithium amide base generates a bicyclic enone containing a pyrrolidinone ring with the relative and absolute stereochemistry of the target. A further 15 synthetic steps, including conjugate cuprate addition to the enone of a side chain precursor, a Ru-promoted oxidation of the phenyl ring to the C2-carboxylic acid substituent, a regioselective Baeyer-Villiger reaction, and an E-selective Horner-Wadsworth-Emmons reaction, elaborate the cyclization product into the target molecule. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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