(Triphenylphosphoranylidene)acetaldehyde → 3-(2-Triethylsilyl-4-furyl)-2-propen-1-al

Participants

Reaction Steps

Reacting 2-triethylsilyl-4-furaldehyde (Compound 5) with (triphenylphosphoranylidene)acetaldehyde gives 3-(2-triethylsilyl-4-furyl)-2-propen-1-al (Compound 45). Conjugate addition of dodecylCu(CN)ZnI (Compound 30) to this aldehyde (Compound 45) gives 4-[1-(2-oxoethyl)tridecyl]-2-triethylsilylfuran (Compound 46). Treatment of this intermediate with manganese dioxide, sodium cyanide and ammonia in tert-butanol, followed by singlet oxygen oxidation gives 4-[1-(2-carboxyamido)methyl]tridecyl-5-hydroxy-2(5H)-furanone (Compound 16).

Provenance & Evidence