123287-92-3

Upstream product

• 101537-87-5 (E)-N-(4,4-diethoxybutyl)-2,3-bis-(3,4-dimethoxyphenyl)-acrylamide 
• 121194-88-5 (E)-2,3-bis-(3,4-dimethoxyphenyl)-N-(3-formylpropyl)acrylamide 
• 52840-52-5 (E)-2,3-bis(3,4-dimethoxyphenyl)acrylic acid 
• 123257-01-2 (E)-(+)-(1'R,3'R,4'S)-8-phenyl-p-menthan-3'-yl 6-<(E)-2,3-bis-(3,4-dimethoxyphenyl)acrylamido>hex-2-enoate 
• 80595-60-4 (-)-phenylmenthyl (triphenylphosphoranylidene)acetate 
• 121194-88-5 (E)-2,3-Bis-(3,4-dimethoxy-phenyl)-N-(4-oxo-butyl)-acrylamide 
• 123257-01-2 (E)-6-[(E)-2,3-Bis-(3,4-dimethoxy-phenyl)-acryloylamino]-hex-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Downstream Products

• 123257-03-4 (13aR,14S,1'R,3'R,4'S)-(-)-8'-phenyl-p-menthan-3'-yl 2,3,6,7-tetramethoxy-9-oxo-9,11,13,13a,14-hexahydrophenanthro<9.10-f>indolizine-14-carboxylate 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of Naturally Occurring (R)-(-)-Enantiomer of Tylophorine via Intramolecular Double Michael Reaction

The first asymmetric total synthesis of the naturally occurring (R)-(-)-enantiomer (1) of tylophorine was achieved with high enantioselectivity via the intramolecular double Michael reaction of α,β-unsaturated esters (10) and (20), having two different chiral auxiliaries, with t-butyldimethylsilyl trifluoromethanesulphonate in the presence of triethylamine. (-)-Phenylmenthol and (2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-5-hydroxy-2-phenyl-1,3-dioxane, readily available from D-glucose, were used as chiral auxiliaries.

Enantioselective synthesis of naturally occurring (-)-tylophorine by way of an asymmetric intramolecular double Michael reaction

Treatment of the 8-phenylmenthyl α, β -unsaturated amide ester (3) with tert.-butyldimethylsilyl trifluoromethanesulfonate and triethylamine produced, with a complete diastereofacial selection, the indolizidines (4), which were converted into (-)-(R)-tylophorine (1).