151166-78-8Relevant articles and documents
Access to Polycyclic Alkaloid-Like Structures by Coupling the Passerini and Ugi Reactions with Two Sequential Metal-Catalyzed Cyclizations
Spallarossa, Martina,Banfi, Luca,Basso, Andrea,Moni, Lisa,Riva, Renata
, p. 2940 - 2948 (2016/09/16)
Complex polycyclic compounds resembling some natural alkaloids have been prepared in only three high yielding steps by combining the Ugi or Passerini multicomponent reactions with two metal-catalyzed cyclizations: an intramolecular Tsuji–Trost reaction of the isocyanide-derived amide followed by a ring-closing metathesis. Scaffold diversity may be explored by the appropriate choice of starting unsaturated isocyanides. The Tsuji–Trost cyclization proceeds with moderate to good diastereoselectivity, and the major diastereomer was in most cases isolated in the pure form. (Figure presented.).
Synthesis of Diverse 6-Oxa-allocolchicinoids by a Suzuki-Miyaura Coupling, Acid-Catalyzed Intramolecular Transacetalization Strategy
Yadav, Dharmendra B.,Taleli, Lebusetsa,Van Der Westhuyzen, Alet E.,Fernandes, Manuel A.,Dragoun, Maxim,Prokop, Aram,Schmalz, Hans-Günther,De Koning, Charles B.,Van Otterlo, Willem A. L.
, p. 5167 - 5182 (2015/08/18)
The synthesis of allocolchicine analogues is of importance as these compounds have been found to possess promising anticancer activity by affecting tubulin polymerization. In this paper, the synthesis of 28 novel substituted 6-oxa-allocolchicinoids is rep
A synthesis of (aR,7S)-(-)-N-acetylcolchinol and its conjugate with a cyclic RGD peptide
Besong, Gilbert,Billen, Denis,Dager, Indu,Kocienski, Philip,Sliwinski, Eric,Tai, Lik Ren,Boyle, F. Thomas
, p. 4700 - 4710 (2008/09/21)
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
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 35-36, (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.
CHEMICAL PROCESSES AND INTERMEDIATES
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Page/Page column 38, (2008/06/13)
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.
