Tetrahedron

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

JE Baldwin, SJ Bamford, AM Fryer, MPW Rudolph…

Index: Baldwin, Jack E.; Bamford, Samantha J.; Fryer, Andrew M.; Rudolph, Martin P. W.; Wood, Mark E. Tetrahedron, 1997 , vol. 53, # 14 p. 5233 - 5254

Full Text: HTML

Citation Number: 37

Abstract

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.