131723-80-3

Upstream product

• 866394-49-2 (R)-1-allyl-3',4'-dimethoxy-2,3-dihydro-[1,1'-biphenyl]-4(1H)-one 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 1108084-55-4 3-ethoxy-6-(3',4'-dimethoxyl-phenyl)cyclohex-2-en-1-one 
• 131652-95-4 1-Benzyl-aziridine-2-carboxylic acid (R)-1-benzyloxymethyl-3-(3,4-dimethoxy-phenyl)-4-(2-nitro-phenylselanyl)-butyl ester 
• 131669-26-6 (3aR,5R,7aR)-5-Benzyloxymethyl-3a-(3,4-dimethoxy-phenyl)-7-oxo-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester 
• 131653-08-2 (2R,3R)-3-(3-Benzyloxy-2-oxo-propyl)-3-(3,4-dimethoxy-phenyl)-2-formyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 131653-07-1 (2R,3R)-3-(3-Benzyloxy-2-hydroxy-propyl)-3-(3,4-dimethoxy-phenyl)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 131652-85-2 (3aR,7aS)-6-Benzyloxy-3a-(3,4-dimethoxy-phenyl)-5-hydroxy-2,3,3a,4,5,7a-hexahydro-indole-1-carboxylic acid benzyl ester 
• 131653-09-3 (3aR,7aS)-6-Benzyloxy-3a-(3,4-dimethoxy-phenyl)-5-oxo-2,3,3a,4,5,7a-hexahydro-indole-1-carboxylic acid benzyl ester 
• 131652-96-5 1-Benzyl-aziridine-2-carboxylic acid (R)-1-benzyloxymethyl-3-(3,4-dimethoxy-phenyl)-but-3-enyl ester 
• 131652-97-6 (3aR,5R,7aR)-1-Benzyl-5-benzyloxymethyl-3a-(3,4-dimethoxy-phenyl)-hexahydro-pyrano[3,4-b]pyrrol-7-one 
• 131652-79-4 (R)-1-Benzyloxy-4-(3,4-dimethoxy-phenyl)-5-(2-nitro-phenylselanyl)-pentan-2-ol 
• 131652-98-7 (3aR,5R,7aR)-5-Benzyloxymethyl-3a-(3,4-dimethoxy-phenyl)-hexahydro-pyrano[3,4-b]pyrrol-7-one 
• 81309-80-0 (R)-5-Benzyloxymethyl-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one 

Relevant academic research and scientific papers

Palladium-catalyzed asymmetric direct intermolecular allylation of α-aryl cyclic vinylogous esters: Divergent synthesis of (+)-oxomaritidine and (?)-mesembrine

We demonstrate that α-aryl cyclic vinylogous esters are competent substrates in the direct intermolecular Pd-catalyzed asymmetric allylic alkylation, enabling a straightforward enantioselective synthesis of 6-allyl-6-aryl-3-ethoxycyclohex-2-en-1-ones, common motifs embedded in numerous structurally diverse natural products. As an initial demonstration of the utility of this protocol, the first catalytic enantioselective total synthesis of (+)-oxomaritidine and an improved five-step catalytic enantioselective synthesis of (?)-mesembrine have been completed divergently.

Enantiospecific Construction of Quaternary Carbon Center via Intramolecular 1,3-Dipolar Cycloaddition. A New Route to Natural (-)-Mesembrine from (S)-O-Benzylglycidol

Thermolysis of the aziridine ester, obtained from (S)-O-benzylglycidol, afforded the pyrrolidine lactone bearing a quaternary carbon center stereo-specifically in a good yield via intramolecular cycloaddition of the 1,3-dipole.The adduct (11) could be converted into natural (-)-mesembrine, the major alkaloid of Sceletium namaquense, and its N-demethyl derivative via a 8 step sequence of reactions.