1388684-77-2

Upstream product

• 90181-25-2 N-<(1,1-dimethylethoxy)carbonyl>-O-<(1,1-dimethylethyl)dimethylsilyl>-D-serine 
• 98-59-9 p-toluenesulfonyl chloride 
• 153527-11-8 (R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dioxo-pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 608128-73-0 (3R,4S,5S,6S)-epi-cis-clausenamide 
• 1388684-99-8 C₂₂H₃₅NO₄Si 
• 1388685-00-4 C₁₈H₂₉NO₂Si 
• 114376-79-3 (4S,5S)-5-hydroxymethyl-1-methyl-4-phenylpyrrolidin-2-one 
• 114376-80-6 C₁₂H₁₃NO₂ 
• 114488-11-8 (+)-3-deoxyepiclausenamide 
• 1388684-83-0 C₂₂H₃₃NO₄Si 

Relevant academic research and scientific papers

Suzuki-Miyaura coupling based enantioselective synthesis of (+)-epi- Clausenamide and the enantiomer of its 3-deoxy analogue

The first enantioselective synthesis of two biologically interesting close analogues of clausenamide, namely (+)-epi-clausenamide and (-)-3-deoxy-epi- clausenamide, was reported. Key steps of the synthesis included construction of the chiral pyrrolinone intermediates from d- and l-serine derivatives, introduction of the C4-phenyl by Suzuki-Miyaura coupling and establishment of the C6 configuration by a threo-selective Grignard reaction. Optimization of the key Suzuki-Miyaura coupling reaction was described in detail. Georg Thieme Verlag Stuttgart · New York.