Determination by enantioselective synthesis of the absolute configuration of CPE, a potential intermediate in coronatine biosynthesis.
The first enantioselective synthesis of the methyl ester of CPE, a potential intermediate in coronatine (COR) biosynthesis, is described. Comparison of the specific rotation of the synthetic ester with that of the methyl ester of natural CPE established that the latter possesses the (R) configuration. This configuration is the same as that found at the corresponding asymmetric center of coronatine. Structure: see text.
Tao
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Department of Chemistry MS60, Rice University, Houston, Texas 77251-1892, USA.
Parry
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D000596:Amino Acids / Q000737:chemistry*; D001427:Bacterial Toxins / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003517:Cyclopentanes / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry; D005285:Fermentation; D007192:Indenes / Q000737:chemistry*; D008968:Molecular Conformation; D011549:Pseudomonas / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D001427:Bacterial Toxins; D003517:Cyclopentanes; D004952:Esters; D007192:Indenes; C449399:cyclopentenone carboxylic acid; C058487:coronatine; C013905:cyclopentenone