886733-89-7

Upstream product

• 62332-68-7 ethyl (2E,4E)-2,4-dimethylhexa-2,4-dienoate 
• 886733-97-7 (R,E)-benzyl 2,4-dimethyl-2-(3-oxopropylthio)hexa-3,5-dienoate 
• 79-03-8 propionyl chloride 
• 241806-94-0 (2E,4E)-2,4-dimethylhexa-2,4-dienoic acid 
• 497-03-0 2-methylbut-2-enal 
• 886733-93-3 (R)-4-benzyl-3-[(2E,4E)-2,4-dimethylhexa-2,4-dienoyl]oxazolidin-2-one 
• 886733-91-1 (R)-4-benzyl-3-[(R,E)-2-(3,3-dimethoxypropylthio)-2,4-dimethylhexa-3,5-dienoyl]oxazolidin-2-one 
• 886733-96-6 (R,E)-benzyl 2-(3,3-dimethoxypropylthio)-2,4-dimethylhexa-3,5-dienoate 

Downstream Products

• 82079-32-1 (+)-thiolactomycin 

Relevant academic research and scientific papers

Efficient synthesis and biological activity of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative

The title total synthesis was achieved by employing deconjugative asymmetric α-sulfenylation of the chiral 3-(α,β,γ,δ-unsaturated acyl)oxazolidin-2-one with a 3,3-dimethoxypropyl methanethiosulfonate as a key step. From the biological activity assay carried out using the title compounds, it appeared evident that in vitro antibacterial and mammalian type I FAS inhibitory activity can be cleanly separated by changing not only the substituent at the C3-position but also the absolute configuration at the C5-position, and that unnatural (S)-(-)-3-demethylthiolactomycin and its congeners might be usable as selective mammalian type I FAS inhibitors.

Efficient synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative

Starting with commercially available tiglic aldehyde, the title synthesis was achieved by employing deconjugative asymmetric α-sulfenylation of the chiral 3-(α,β,γ,δ-unsaturated acyl)-2-oxazolidinone with a methanethiosulfonate as a key step.