108102-81-4Relevant articles and documents
Synthesis of Novel Dibenzylbutyrolactones as Dimethylmatairesinol Analogues
Heidary Alizadeh, Babak,Foroumadi, Alireza,Kobarfard, Farzad,Saeedi, Mina,Shafiee, Abbas
, p. 1693 - 1698 (2015/11/09)
In this work, (R)-4-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one was prepared though an efficient and novel method starting from (S)-5-((benzyloxy)methyl)dihydrofuran-2(3H)-one. Then, it was utilized as a versatile starting material for the synthesis of novel dimethylmatairesinol analogues; dibenzylbutyrolactone derivatives, via the reaction of the later compound and various aromatic aldehydes.
Asymmetric Synthesis of Dibenzylbutyrolactones and Aryltetralin Lignan Lactones by Tandem Cojugate Addition to a Chiral Butenolide
Pelter, Andrew,Ward, Robert S.,Jones, D. Martin,Maddocks, Peter
, p. 2621 - 2630 (2007/10/02)
Addition of sulfur-stabilised carbanions to (-)-5-(1-menthyloxy)furan-2(5H)-one followed by reaction with an aromatic aldehyde affords a short synthesis of enantiomerically pure dibenzylbutyrolactone derivatives.Desulfurisation with NaBH4/NiCl2 proceeds in almost quantitative yield, and reduction with NaBH4/KOH gives the parent dibenzylbutyrolactones including (-)-6-epi-podorhizol.These undergo cyclisation with acid to give homochiral aryltetralines including (-)-deoxyisopodophyllotoxin in high yield.
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.
(R)-(+)-β-VERATRYL-γ-BUTYROLACTONE, A NEW KEY-INTERMEDIATE FOR THE ASYMMETRIC SYNTHESIS OF VARIOUS LIGNANS
Brown, Eric,Daugan, Alain
, p. 3719 - 3722 (2007/10/02)
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
Synthesis of Aryltetralin and Dibenzylbutyrolactone Lignans: (+/-)-Lintetralin, (+/-)-Phyltetralin, and (+/-)-Kusunokinin
Ganeshpure, Pralhad A.,Stevenson, Robert
, p. 1681 - 1684 (2007/10/02)
Application of a general synthetic pathway for aryltetralin and dibenzylbutyrolactone lignans, starting from the lithium enolate of 3-(3,4-dimethoxybenzyl)butyrolactone (1) led to syntheses of (+/-)-lintetralin (4), (+/-)-phyltetralin (5), (+/-)-isogalcat
