86853-06-7

Upstream product

• 67-56-1 methanol 
• 89812-55-5 (E)-2-Methyl-1,1-bis-methylsulfanyl-5-phenyl-penta-1,4-dien-3-one 
• 67498-12-8 (E)-(2S,3S)-3-Hydroxy-2-methyl-5-phenyl-pent-4-enoic acid methyl ester 
• 67498-12-8 (E)-syn-methyl 3-hydroxy-2-methyl-5-phenyl-4-pentanoate 
• 90784-73-9 γ-bromo-α-methyl-acetessigsaeuremethylester 
• 14371-10-9 (E)-3-phenylpropenal 
• 100-52-7 benzaldehyde 
• 90784-76-2 Methyl 4-(diphenylphosphinoyl)-2-methyl-3-oxobutanoate 

Downstream Products

• 1087752-99-5 (E)-methyl 3-hydroxy-2-methyl-5-phenylpent-4-enoate 
• 1087752-99-5 (E)-methyl 3-hydroxy-2-methyl-5-phenylpent-4-enoate 
• 86853-07-8 (2S,3R,4E)-(+)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester 
• 67498-12-8 (E)-(2S,3S)-3-Hydroxy-2-methyl-5-phenyl-pent-4-enoic acid methyl ester 
• 67498-12-8 (E)-syn-methyl 3-hydroxy-2-methyl-5-phenyl-4-pentanoate 
• 82414-48-0 (E)-(2S,3R)-3-Methoxy-2-methyl-5-phenyl-pent-4-enoic acid 
• 82414-47-9 (E)-(2S,3R)-3-Methoxy-2-methyl-5-phenyl-pent-4-enoic acid methyl ester 
• 82414-51-5 (E)-(2S,3S)-2-Methyl-5-phenyl-pent-4-ene-1,3-diol 
• 88155-83-3 methyl (E)-(3R^*,4S^*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate 
• 73341-71-6 (+/-)-oudemansin A 
• 73341-71-6 oudemansin A 
• 86838-35-9 (E)-(2S,3R)-2-Methyl-5-phenyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-pent-4-enoic acid methyl ester 
• 107184-56-5 (E)-(2S,3R)-3-Acetoxy-2-methyl-5-phenyl-pent-4-enoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of Methyl 5-Aryl-3-oxo-4-pentenoates and Novel Substituted Cyclopentenones

The cinnamoyl- (1a-j) and (5-phenyl-2,4-pentadienoyl)- (1k) ketene dithioacetals are shown to undergo methanolysis in the presence of ether-boron trifluoride complex and mercury(II) chloride to the corresponding methyl 5-aryl-3-oxo-4-pentenoates 2a-j and 3-oxo-7-phenyl-4,6-heptadienoate (2k), respectively, in good yields.However, the corresponding (2-methylcinnamoyl)ketene dithioacetals 3a-f, under identical reaction conditions, undergo Nazarov cyclization to give the corresponding substituted cyclopentenones 4a-f.

Synthesis of α-substituted γ,δ-unsatured β-oxo esters

Two approaches to the synthesis of the title compounds 3 are described.The first consist of direct alkylation of the unsatured β-oxo esters 1 via their monoanions.The best results were obtained using the heterogeneous sodium methoxide/alumina system.Isolation of pure, mono-α-alkylated compounds requires chromatographic separation of the reaction products.The second approach makes use of the Horner-Wittig reaction. α-substituted phosphine oxides 4 were converted into their dianions and reacted with aldehydes and ketones to afford the mono-α-alkylated β-oxo esters 3 in good yields.The requisite phosphine oxides were obtained from the corresponding γ-bromo β-oxo esters 10 via an Arbusov reaction with ethyl diphenylphosphinite.Finally, it was found that α,α-dialkylated and α,α,γ-trialkylated β-oxo esters 8 and 15 can be obtained by reaction of 1 with an excess of alkyl halide in the presence of two or four equivalents of sodium hydride, respectively.