140223-75-2

Upstream product

• 77934-87-3 (5R)-menthyloxy-2<5H>-furanone 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 108-98-5 thiophenol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 60354-22-5 4-[Bis(phenylsulfanyl)methyl]-1,2-dimethoxybenzene 
• 112968-75-9 (5R)-(L-menthyloxy)-2(5H)-furanone 

Downstream Products

• 135588-81-7 (3R,4R,5R)-3,4-Bis-(3,4-dimethoxy-benzyl)-5-(2-isopropyl-5-methyl-cyclohexyloxy)-dihydro-furan-2-one 
• 58311-18-5 (2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol 
• 25488-59-9 dimethylmatairesinol 
• 140223-76-3 (-)-(3S,4R,5R)-3,4-bis(3',4'-dimethoxybenzyl)-5-(1-menthyloxy)butyrolactone 

Relevant academic research and scientific papers

Enantioselective synthesis of natural dibenzylbutyrolactone lignans (-)-enterolactone, (-)-hinokinin, (-)-pluviatolide, (-)-enterodiol, and furofuran lignan (-)-eudesmin via tandem conjugate addition to γ-alkoxybutenolides1,2

A general and efficient method is described for the asymmetric synthesis of a variety of liguans. 5-(Menthyloxy)-2(5H)-furanones 5 proved to be excellent chiral synthons in this respect and could be transformed with complete stereoselectivity into a number of lignans. The addition of lithiated dithianes 7 to enantiomerically pure butenolides 5 was followed by quenching of the resulting lactone enolate anions with a benzylbromide (9) or with an aldehyde (6). This tandem addition quenching procedure gave the diastereomerically pure adducts 11, 26, or 27 in 50-67% yield, with a carbon skeleton as found in most natural lignans. As examples of the wide applicability of this method, the syntheses of the enantiomerically pure natural lignans (-)-hinokinin (23b), (-)-enterolactone (24a), (-)-pluviatolide (24c), and (-)-enterodiol (25) in overall yields of 29-37% from 5a and (-)eudesmin (30) in 16% overall yield from 5b are described.

Asymmetric Synthesis of Lignans of the Dibenzylbutanediol and Tetrahydrodibenzocyclooctene Series

Enolate anions obtained by conjugate addition to (-)-5-(1-menthyloxy)furan-2(5H)-one are quenched with benzyl bromides or iodides to yield homochiral dibenzylbutyrolactones.Desufurisation followed by lithium aluminium hydride reduction affords homochiral

Asymmetric Syntheses of Lignans of the Dibenzylbutyrolactone, Dibenzylbutanediol, Aryltetralin and Dibenzocyclooctadiene Series

General procedures are outlined for the asymmetric syntheses of ligands of the dibenzylbutyrolactone, dibenzylbutanediol, aryltetralin and dibenzocyclooctadiene series, from tandem addition products derived from 4-mentyloxybutenolide.