135965-91-2Relevant academic research and scientific papers
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.
