111042-75-2

Upstream product

• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 601-75-2 ethylmalonic acid 
• 2216-51-5 (-)-menthol 

Downstream Products

• 111042-77-4 (2S)-2-(dimethyl-t-butylsiloxymethyl)butyl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropionate 
• 122778-49-8 (S)-2-Chloromethyl-butyric acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 72447-52-0 (S)-2-Methyl-butyric acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 122778-44-3 (1R,3R,4S)-p-menthan-3-yl (2R)-2-(dimethyl-t-butylsiloxymethyl)butyrate 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 111137-99-6 (S)-α-Methoxy-α-(trifluormethyl)phenylessigsaeure-(S)-(2-methylbutyl)ester 
• 111070-64-5 (1R,3R,4S)-p-menthan-3-yl (2R)-2-hydroxymethylbutyrate 

Relevant academic research and scientific papers

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).

Asymmetric Syntheses of Chiral Propane-1,3-diols Starting from Malonic Acid

Syntheses of chiral intermediates having one tertiary asymmetric centre were carried out via chiral half-esters of monoalkylmalonic acids.The menthyl half-ester of ethylmalonic acid afforded a single diastereoisomer through crystallisation-induced asymmetric transformation (second-order asymmertic transformation).Furthermore enantioselective preparation of unsymmertical propane-1,3-diol derivatives was achieved by the use of 8-phenylmenthyl half-esters.

Enantioselective Synthesis of Useful Chiral Precursors, Unsymmetrical Propane-1,3-diol Derivatives, from Malonic acid

Syntheses of chiral synthons via monosubstituted malonic chiral half esters were studied and chiral 3-silyloxy propanols were enantioselectively synthesised.