132697-68-8

Upstream product

• 120-57-0 piperonal 
• 112968-75-9 (5R)-(L-menthyloxy)-2(5H)-furanone 
• 132635-99-5 lithio 3,4-dimethoxybenzyl phenyl sulphide 
• 83318-94-9 (3,4-dimethoxybenzyl)(phenyl)sulfane 
• 2216-51-5 (-)-menthol 
• 112968-75-9 (+)-(5S)-5-((+)-menthyl)oxy-2<5H>-furanone 

Downstream Products

• 132635-98-4 (-)-(3S,4R,5R,6R)-3-(3',4'-methylenedioxy-α-hydroxybenzyl)-4-<3'',4''-dimethoxybenzyl>-5-(1-menthyloxy)butyrolactone 

Relevant academic research and scientific papers

ASYMMETRIC SYNTHESIS OF HOMOCHIRAL DIBENZYLBUTYROLACTONE LIGNANS BY CONJUGATE ADDITION TO A CHIRAL BUTENOLIDE

Addition of sulphur stabilised carbanions to a chiral non-racemic butenolide followed by reaction with an aromatic aldehyde affords a short synthesis of homochiral dibenzylbutyrolactone derivatives.Desulphurisation of the first formed adducts proceeds in almost quantitative yield to afford the parent lignan.

Asymmetric Synthesis of Dibenzylbutyrolactones and Aryltetralin Lignan Lactones by Tandem Cojugate Addition to a Chiral Butenolide

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.