166193-97-1Relevant academic research and scientific papers
Asymmetric organocatalytic intramolecular aza-michael addition of enone carbamates: Catalytic enantioselective access to functionalized 2-substituted piperidines
Liu, Jian-Dong,Chen, Ying-Chun,Zhang, Guo-Biao,Li, Zhi-Qiang,Chen, Peng,Du, Ji-Yuan,Tu, Yong-Qiang,Fan, Chun-An
supporting information; experimental part, p. 2721 - 2730 (2011/12/04)
The synthetically useful functionalized 2-substituted piperidines containing a lateral ketone group have been strategically accessed via an organocatalytic enantioselective intramolecular aza-Michael addition of enone carbamates, in which a novel internal substrate combination of the enone moiety as Michael acceptor and the carbamate moiety as Michael donor was revealed in asymmetric bifunctional organocatalysis. This heteroatom conjugate addition, which was realized by using a catalytic chiral Cinchona-based primary-tertiary diamine and an achiral Bronsted acid, mostly proceeded in high yield and good to excellent stereocontrol (up to 99% ee). This reaction provides an alternative catalytic asymmetric method for installing the stereogenic nitrogen-containing carbon center in functionalized 2-substituted piperidines, leading to the development of a straightforward and expeditious synthesis of some naturally occurring bioactive 2-substituted piperidine alkaloids. Copyright
Synthesis of a metabolite of an anti-angiogenic lead candidate based on a d-glucosamine motif
Singh, Latika,Lam, Ann,Premraj, Rajaratnam,Seifert, Joachim
, p. 4854 - 4856 (2008/09/21)
A rapid synthetic access to ACL 21269 was established in 12 steps starting from thiogylcoside 9 utilizing synthons 8 and 6 to introduce the pharmacophores at positions 1 and 2. The functional groups decorating the glucosamine scaffold were introduced in a particular order and common protecting groups were employed to establish a robust synthetic process.
Synthesis and Biochemical Evaluation of Adenosylspermidine, a Nucleoside-Polyamine Adduct Inhibitor of Spermidine Synthase
Lakanen, John R.,Pegg, Anthony E.,Coward, James K.
, p. 2714 - 2727 (2007/10/03)
The synthesis of a new class of multisubstrate adduct inhibitors of polyamine biosynthesis has been investigated.The first target compound, designed to inhibit spermidine synthase, was obtained and proved to be a very potent inhibitor of that enzyme.Two s
