17187-78-9Relevant articles and documents
Stereoselective reactions. X. Total synthesis of optically pure antitumor lignan, burseran
Tomioka,Ishiguro,Koga
, p. 4333 - 4337 (1985)
-
Diastereoselective synthesis of β-piperonyl-γ-butyrolactones from Morita-Baylis-Hillman adducts. highly efficient synthesis of (±)-yatein, (±)-podorhizol and (±)-epi-podorhizol
Trazzi, Giordano,Andre?, Marcelo Fabiano,Coelho, Fernando
experimental part, p. 2327 - 2339 (2011/10/09)
Starting from a Morita-Baylis-Hillman adduct we describe a simple and very efficient method for the diastereoselective preparation of hydroxylated β-piperonyl-γ-butyrolactones. To exemplify the efficiency of this approach we also describe a highly efficie
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.