Tetrahedron

Lignames: 10. Preparation des (R)-(+) et (S)-(−)-β-piperonyl et β-veratryl-γ-butyrolactones et leur utilisation dans la synthese totale de lignanes optiquement actifs

E Brown, A Daugan

Index: Brown, Eric; Daugan, Alain Tetrahedron, 1989 ,  vol. 45,  # 1  p. 141 - 154

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Citation Number: 40

Abstract

A simple and efficient route leading to optically active β-benzyl-γ-butyrolactones is described. Thus, the methyl (R, S)-α-benzylheBisuccinate resulting from a Stobbe condensation with an appropriate aromatic aldehyde, followed by catalytic hydrogenation of the intermediate α-benzylidene hemisuccinic ester, was resolved by means of a chiral base (ephedrine or α-inethyl benzy lamine). Reduction of each enantiomer, using calcium ...