Towards a versatile synthesis of kainoids I: Introduction of the C-3 and C-4 substituents

Article abstract of DOI:10.1016/S0040-4020(97)00190-7

The first stages in the synthesis of acromelic acid analogues from trans-4-hydroxy-L-proline are described. An enamine alkylation was used to stereospecifically introduce the C-3 substituent, Grignard addition to a ketone or Pd(0) catalysed cross-coupling procedures adding C-4 aryl substituents for further manipulation. A number of versatile intermediates were generated.