122937-65-9

Upstream product

• 122937-64-8 (+)-(3S,4R)-3-(2-Benzyloxyethyl)-N-(3,4-dimethoxyphenethyl)-4-hydroxymethylhexacarboxamide 
• 123001-19-4 (-)-Ethyl (4R)-(E)-4-Hydroxymethylhex-2-enoate 
• 131815-04-8 (S)-2-(2-Bromo-1-ethoxy-ethoxymethyl)-butyraldehyde 
• 122937-66-0 ethyl (2E,4R)-4-(tert-butyldimethylsilyloxymethyl)-2-hexenoate 
• 131815-09-3 2-((4S,5R)-2-Ethoxy-5-ethyl-tetrahydro-pyran-4-yl)-ethanol 
• 131815-05-9 (2R)-2-(tert-butyldimethylsilyloxymethyl)butyraldehyde 
• 115698-60-7 (4S,5R)-4-(2-Benzyloxy-ethyl)-5-ethyl-tetrahydro-pyran-2-ol 
• 123001-21-8 (+)-(4S,5R)-4-(2-Benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone 
• 122937-58-0 (+)-(1S,3S,4R)-p-Menthan-3-yl Hydrogen (S)-Ethylmalonate 
• 122937-59-1 (+)-(1S,3S,4R)-p-Menthan-3-yl (2S)-2-(t-Butyldimethylsiloxymethyl)butyrate 
• 122937-61-5 (R)-2-(2-Bromo-1-ethoxy-ethoxymethyl)-butan-1-ol 
• 111042-76-3 (-)-(2S)-2-((tert-Butyldimethylsiloxy)methyl)butan-1-ol 
• 122937-62-6 (Z)-(R)-4-(2-Bromo-1-ethoxy-ethoxymethyl)-hex-2-enoic acid methyl ester 
• 1325690-29-6 C₁₉H₂₆O₆ 

Downstream Products

• 549-91-7 (-)-Protoemetine 

Relevant academic research and scientific papers

Organocatalytic approach for the syntheses of corynantheidol, dihydrocorynantheol, protoemetinol, protoemetine, and mitragynine

O-Trimethylsilyl (TMS)-protected diphenylprolinol-catalyzed Michael addition of a functionalized alkylidene malonate and n-butanal affords an aldehyde. This adduct can serve as the common intermediate for the assembly of secologanin tryptamine and dopamin

Asymmetric Total Synthesis of (-)-Protoemetinol, (-)-Protoemetine, (-)-Emetine, and (-)-Tubulosine by Highly Stereocontrolled Radical Cyclisations

Both enantiomers of the menthyl half-esters (10) and (23) of ethylmalonic acid were converted into (+)-(4S,5R)-4-(2-benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone (18).A mixture of the trans-(18) and cis-lactones (19) in a ratio of ca. 4:1 was prepared by way of radical cyclisation of the (E)-α,β-unsaturated esters (16), while the former (18) was synthesised with high stereoselection by the cyclisation of the (Z)-esters (26).The lactone (18) was enantioselectively transformed into (-)-protoemetinol (5) and (-)-protoemetine (4), correlated to (-)-emetine (1) and (-)-tubulosine (3).

HIGHLY ENANTIOCONTROLLED TOTAL SYNTHESYS OF (-)-PROTOEMETINOL

Enantiomerically pure (-)-protoemetinol (1) was selectively synthesized from ethylmalonic acid via radical cyclization of the (Z)-α,β-unsaturated ester (12).