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

Orellana, Arturo; Pandey, Sushil K.; Carret, Sébastien; Greene, Andrew E.; Poisson, Jean-François

doi:10.1021/jo300608g.s001

jo300608g_si_001.pdf (2.75 MB)

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

journal contribution

posted on 2012-06-15, 00:00 authored by Arturo Orellana, Sushil K. Pandey, Sébastien Carret, Andrew E. Greene, Jean-François Poisson

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.