894762-73-3

Upstream product

• 894762-72-2 4-benzyloxy-2-[1,1-(ethylenedioxy)ethyl]-bromobenzne 
• 894797-93-4 2-(5-benzyloxy-2-bromo-phenyl)-2-methyl-[1,3]oxathiolane 
• 894762-68-6 4'-benzyloxy-2'-[1,1-(ethylenedioxy)ethyl]-4,5,6-trimethoxy-biphenyl-2-carbaldehyde 
• 894797-87-6 4'-benzyloxy-4,5,6-trimethoxy-2'-(2-methyl-[1,3]oxathiolan-2-yl)-biphenyI-2-carbaldehyde 
• 894797-91-2 2-acetyl-4-benzyloxyphenylboronic acid 
• 35274-53-4 2-bromo-3,4,5-tri-methoxybenzaldehyde 
• 34068-01-4 1-[3-(phenylmethoxy)phenyl]ethan-1-one 
• 894797-89-8 2'-acetyl-4'-benzyloxy-4,5,6-trimethoxybiphenyl-2-carbaldehyde 
• 69138-97-2 2-iodo-3,4,5-trimethoxybenzaldehyde cyclohexylimine 
• 73252-56-9 (2-bromo-3,4,5-trimethoxy-benzylidene)-cyclohexylamine 
• 73252-53-6 3,4,5-trimethoxy-2-iodobenzaldehyde 
• 105805-16-1 1-[2-bromo-5-(phenylmethoxy)phenyl]ethanone 
• 100-44-7 benzyl chloride 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 

Downstream Products

• 1035933-62-0 3-benzyloxy-9,10,11-trimethoxy-6,7-dihydro-dibenzo[a,c]cyclohepten-5-one 

Relevant academic research and scientific papers

A synthesis of (aR,7S)-(-)-N-acetylcolchinol and its conjugate with a cyclic RGD peptide

An asymmetric synthesis of (-)-N-acetylcolchinol is described based on a Suzuki-Miyaura coupling to generate the biaryl pharmacophore. The sole asymmetric centre was introduced by an asymmetric reduction of a dibenzosuberone derivative 24 using lithium bo

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.

CHEMICAL PROCESSES FOR THE PREPARATION OF A COLCHINOL DERIVATIVE AND INTERMEDIATES

A process for the preparation of a colchinol derivative of the Formula (I): wherein each R, which may be the same or different, is selected from (1-6C)alkyl, benzyl and C(O)(1-6C)alkyl, or two RO groups together form a (1-4C)alkylenedioxy group and Ac is acetyl, by reduction of the corresponding enamide of formula (II): Colchinol derivatives with high enantiomeric purity are obtained by hydrogenation in the presence of a transition metal catalyst, particularly a catalyst selected from a rhodium complex, a ruthenium complex or an iridium complex. Novel compounds of formula (II'): wherein each R, which may be the same or different, is selected from (1-6C)alkyl, benzyl and C(O)(1-6C)alkyl, or two RO groups together form a (1-4C)alkylenedioxy group, and P is hydrogen or a suitable hydroxy protecting group are also described.