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A Diels-Alder-based total synthesis of (-)-kainic acid.

The Journal of organic chemistry (2012-05-04)
Arturo Orellana, Sushil K Pandey, Sébastien Carret, Andrew E Greene, Jean-François Poisson
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Malonic acid, ReagentPlus®, 99%
Supelco
Malonic acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Sigma-Aldrich
Sodium malonate dibasic, ≥97.0% (NT)