A Diels–Alder-Based Total Synthesis of (−)-Kainic Acid

• Published in: Journal of organic chemistry Vol. 77; no. 12; pp. 5286 - 5296
• Main Authors: Orellana, Arturo, Pandey, Sushil K, Carret, Sébastien, Greene, Andrew E, Poisson, Jean-François
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 15.06.2012; Amer Chemical Soc
• Subjects: Chemical Sciences; Chemistry; Chemistry, Organic; Cyclization; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Hydroxyproline - chemistry; Kainic Acid - chemical synthesis; Kainic Acid - chemistry; Malonates - chemistry; Molecular Structure; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; HIGH-PRESSURE; FORMAL SYNTHESIS; STEREOCONTROLLED TOTAL-SYNTHESIS; (-)-ALPHA-KAINIC ACID; ALPHA-KAINIC ACID; ENANTIOSPECIFIC TOTAL-SYNTHESIS; CHIRAL LITHIUM AMIDES; (+)-ALPHA-ALLOKAINIC ACID; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; Nitrogen heterocycle; Hydroxyproline; Diels Alder addition; Natural compound; Total synthesis; High pressure; Proline derivative; Stereoselectivity; α-Aminoacid; Cycloaddition; Malonic acid derivatives; Aminoacid; Vinylic compound; Bicyclic compound; Chemical synthesis; Kainic acid; Diels-Alder; cycloaddition
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo300608g

An efficient synthesis of (−)-kainic acid, through a high-pressure-promoted Diels–Alder cycloaddition of a vinylogous malonate derived from 4-hydroxyproline, is described. The bicyclic adduct could be converted into the natural product with complete stereocontrol.