1026478-79-4

Upstream product

• 403656-66-6 (4R)-4-(diphenylmethyl)-3-[(3R)-3-(ethoxycarbonyl)-4-(3',4'-dimethoxyphenyl)]butanoyl-2-oxazolidinone 

Downstream Products

• 123251-05-8 (3R,4R)-3-[(3-methoxy-4-benzyloxyphenyl)methyl]-4-[(3,4-dimethoxyphenyl)methyl] dihydro-2-(3H)-furanone 
• 87605-56-9 (3R,4R)-3-[(3-methoxy-4-hydroxyphenyl)methyl]-4-[(3,4-dimethoxyphenyl)methyl]dihydro-2(3H)-furanone 
• 403805-11-8 (3R,4R)-3-[(3,4-dimethoxyphenyl)methyl]-4-[(3-methoxy-4-benzyloxyphenyl)methyl] dihydro-2-(3H)-furanone 
• 1026565-45-6 (2R,3R)-2-[(3'-methoxy-4'-benzyloxyphenyl)methyl]-3-[(3',4'-dimethoxyphenyl)methyl]-succinic-acid-4-ethyl-ester 

Relevant academic research and scientific papers

Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-Enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid

Lewis acid-mediated conjugate addition of alkyl radicals to a differentially protected fumarate 10 produced the monoalkylated succinates with high chemical efficiency and excellent stereoselectivity. A subsequent alkylation or an aldol reaction furnished the disubstituted succinates with syn configuration. The chiral auxiliary, 4-diphenylmethyl-2-oxazolidinone, controlled the stereoselectivity in both steps. Manipulation of the disubstituted succinates obtained by alkylation furnished the natural products (-)-enterolactone, (-)-arctigenin, and (-)-isoarctigenin. The overall yields for the target natural products were 20-26% over six steps. Selective functionalization of the disubstituted succinates obtained by aldol condensation gave the paraconic acid natural products (-)-nephrosteranic acid (8) and (-)-roccellaric acid (9). The overall yield of the natural products 8 and 9 over four steps was 53% and 42%, respectively.