135191-51-4

Upstream product

• 100-44-7 benzyl chloride 
• 135191-45-6 (S)-5-((2R,3R)-3-Benzyloxymethyl-oxiranyl)-4-(2-methoxy-ethoxymethoxy)-pentanal 
• 135191-44-5 (2R,3R)-2-Benzyloxymethyl-3-[(S)-2-(2-methoxy-ethoxymethoxy)-6-methyl-hept-5-enyl]-oxirane 
• 135191-47-8 N,N-dimethyl-(1R,2R,4R)-2-<(S)-1-hydroxy-2-(phenylmethoxy)ethyl>-4-<(2-methoxyethoxy)methoxy>cyclopentanecarboxamide 
• 135191-43-4 {3-[2-(2-Methoxy-ethoxymethoxy)-6-methyl-hept-5-enyl]-oxiranyl}-methanol 
• 135191-46-7 N,N-dimethyl-(1S,2R)-β-<(S)-(2-methoxyethoxy)methoxy>-2-<(phenylmethoxy)methyl>oxiranepentanamide 

Relevant academic research and scientific papers

Cyclopentane construction with control of side chain configuration synthesis of (+)-brefeldin A

Intramolecular opening of an enantiomerically pure epoxide by an amide enolate (1 → 2) is shown to be an effective method for cyclopentane construction with control of both ring and side chain absolute configuration. This opening serves as the key step in a synthesis of the Golgi apparatus-blocking macrolide (+)-brefeldin A (3). Other features of the synthesis include improved procedures for the enantioselective hydrogenation of a β-keto ester to the corresponding β-hydroxy ester, and for the Julia-Lythgoe reduction of a β-acetoxy sulfone to the trans alkene.