894797-93-4

Upstream product

• 105805-16-1 1-[2-bromo-5-(phenylmethoxy)phenyl]ethanone 
• 60-24-2 2-hydroxyethanethiol 
• 100-44-7 benzyl chloride 
• 121-71-1 3-Hydroxyacetophenone 
• 34068-01-4 1-[3-(phenylmethoxy)phenyl]ethan-1-one 

Downstream Products

• 894797-87-6 4'-benzyloxy-4,5,6-trimethoxy-2'-(2-methyl-[1,3]oxathiolan-2-yl)-biphenyI-2-carbaldehyde 
• 894797-89-8 2'-acetyl-4'-benzyloxy-4,5,6-trimethoxybiphenyl-2-carbaldehyde 
• 894762-73-3 3-benzyloxy-9,10,11-trimethoxy-dibenzo[a,c]cyclohepten-5-one 

Relevant academic research and scientific papers

Asymmetric synthesis of (S)-(-)-N-acetylcolchinol via Ullmann biaryl coupling

A modified Ziegler Ullmann coupling process has been developed as the key step in an effective synthesis of (S)-(-)-N-acetylcolchinol, analogues of which are selective vascular targeting agents with potential importance in cancer chemotherapy. Asymmetric induction is achieved by enamide hydrogenation using FerroTANE catalysts.

CHEMICAL PROCESSES AND INTERMEDIATES

The present invention provides a process for the formation of an enamide (III) wherein each R is independently selected from (1-6C)alkyl, benzyl and C(O)(1-6C)alkyl, or two RO groups together form a (1-4C)alkylenedioxy group, comprising the steps of reductive acylation of an oxime of formula (IX) wherein each R is independently selected from (1-6C)alkyl, benzyl and C(O)(1-6C)alkyl, or two RO groups together form a (1-4C)alkylenedioxy group, and the hydroxy group may optionally be protected by a hydroxy protecting group; and thereafter if necessary, removal of any protecting groups. Intermediates to the enamide (III) and methods for their preparation are also described.