119239-40-6

Upstream product

• 165673-39-2 (E)-3-(methoxycarbonyl)-4-(3,4,5-trimethoxy-phenyl)but-3-enoic acid 
• 119138-93-1 (+/-)-4-(3,4,5-trimethoxyphenyl)-3-methoxycarbonylbutanoic acid 

Downstream Products

• 119138-76-0 (3R,4R)-3-(4-Benzyloxy-3-methoxy-benzyl)-4-(3,4,5-trimethoxy-benzyl)-dihydro-furan-2-one 
• 101751-71-7 (-)-cubebinone 
• 119138-77-1 2R,3R,2-(7-methoxy 1,3-benzodioxol-5-yl) methyl 3-(3,4,5-trimethoxyphenyl) methyl butan-1,4-diol 
• 101751-72-8 (-)-isoyatein 
• 93395-16-5 (-)-Cubebininolide 
• 79288-73-6 (2R,3R)-2-4-hydroxy-3-methoxybenzyl-3-3',4',5'-trimethoxybenzylbutyrolactone 
• 73149-51-6 (-)-Dihydroclusin 
• 64767-71-1 2-3,4-dimethoxybenzyl-3-3',4',5'-trimethoxybenzylbutyrolactone 
• 76763-88-7 (R)-dihydro-4-(3,4,5-trimethoxybenzyl)furan-2(3H)-one 

Relevant academic research and scientific papers

Synthesis of optically pure gomisi lignans: The total synthesis of (+)-schizandrin, (+)-gomisin A, and (+)-isoschizandrin in naturally occurring forms

The total syntheses of (+)-schizandrin (1), (+)-gomisin A (2), and (+)-isoschizandrin (3) having natural configurations were accomplished. Optically pure butyrolactones ((-)-9, (-)-31) were transformed to α-benzylidenebutyrolactones ((+)-10, (+)-32, (+)-35). By a highly efficient iron(III) perchlorate-mediated oxidative coupling reaction of 10, 32, and 35, the key intermediates with biphenyl skeletons ((-)-11, (-)-33) were constructed with high stereoselectivity. Several methods for the stereoselective introduction of the C6-hydroxyl group were examined. For the synthesis of schizandrin and gomisin A, the Mukaiyama hydration reaction of (-)-11 and(-)-33 provided the desired products with satisfactory selectivity. For the synthesis of isoschizandrin, the stereoselective epoxidation of allylic alcohol (+)-48 was successfully utilized taking advantage of its conformational features.

Total Synthesis of Homochiral Kadsurin Having the Natural Configuration

The total synthesis of kadsurin was achieved in a stereoselective manner.The stereoselective hydrogenation of the homochiral enone (12), obtained from the known tetracyclic lactone (7), afforded known ketone (13), the conversion of which into kadsurin has

A SIMPLE PREPARATION OF (R)-(+)-β-(3,4,5-TRIMETHOXYBENZYL)-BUTANOLIDE, AND ITS USE IN THE TOTAL SYNTHESES OF NATURALLY OCCURRING DIBENZYLBUTANOLIDE LIGNANS

Resolution of methyl α-(3,4,5-trimethoxybenzyl)hemisuccinate by means of (-)-ephedrine, followed by calcium borohydride reduction, afforded (R)-(+)-β-(3,4,5-trimethoxybenzyl)butanolide.This lactone was used as a starting material for the optically active