67533-86-2Relevant academic research and scientific papers
(R)-(+)-β-VERATRYL-γ-BUTYROLACTONE, A NEW KEY-INTERMEDIATE FOR THE ASYMMETRIC SYNTHESIS OF VARIOUS LIGNANS
Brown, Eric,Daugan, Alain
, p. 3719 - 3722 (1986)
Methyl α-veratrylhemisuccinate was resolved into its (R)-(+) and (S)-(-) antipodes by (S)-(-) and (R)-(+)-α-methylbenzylamine respectively.Calcium borohydride reduction of the (R)-(+)-hemiester afforded (R)-(+)-β-veratryl-γ-butyrolactone.The latter was us
LIGNANES.10. PREPARATION DES (R)-(+) ET (S)-(-)-β-PIPERONYL ET β-VERATRYL-γ-BUTYROLACTONES ET LEUR UTILISATION DANS LA SYNTHESE TOTALE DE LIGNANES OPTIQUEMENT ACTIFS
Brown, Eric,Daugan, Alain
, p. 141 - 154 (2007/10/02)
A simple and efficient route leading to optically active β-benzyl-γ-butyrolactones is described.Thus, the methyl (R,S)-α-benzylhemisuccinate 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-methyl benzylamine).Reduction of each enantiomer, using calcium borohydride, then led to the corresponding optically active β-benzyl-γ-butyrolactone.In this way, the following two lactones were obtained in both (R)-(+) and (S)-(-) enantiomeric forms, β-piperonyl- and β-veratryl-γ-butyrolactones 1 and 2 respectively.These lactones were used as key-intermediates for the syntheses of 17 optically active lignans and lignoids, such as (-)-dimethylmatairesinol (-)-23, (-)-kusunokinin (-)-26 and (+)-dimethylisolariciresinol (+)-35.
