894762-72-2Relevant academic research and scientific papers
Asymmetric synthesis of (S)-(-)-N-acetylcolchinol via Ullmann biaryl coupling
Broady, Simon D.,Golden, Michael D.,Leonard, John,Muir, James C.,Maudet, Mickael
, p. 4627 - 4630 (2008/02/06)
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 FOR THE PREPARATION OF A COLCHINOL DERIVATIVE AND INTERMEDIATES
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Page/Page column 34, (2008/06/13)
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.
