Univerzita Pardubice Fakulta chemicko- technologická

Univerzita Pardubice

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English

Publikace detail

Preparation of Clavaminol A and Xestoaminol C via asymmetric Henry reaction

Autoři: Drabina Pavel | Nováková Gabriela | Sedlák Miloš

Rok: 2018

Druh publikace: ostatní - přednáška nebo poster

Strana od-do: nestránkováno

Tituly:

Jazyk	Název	Abstrakt	Klíčová slova
eng	Preparation of Clavaminol A and Xestoaminol C via asymmetric Henry reaction	1-Deoxysphingolipids such as Clavaminols A–N, Xestoaminols A–C, Spisulosine and Obscuraminols A-F belong to the group of sphingolipids, which represent an important class of natural products derived from the essential sphingoid base d-erythro-sphingosine [1]. Sphingolipids are ubiquitous components of eukaryotic cell membranes and are found in diverse organisms from fungi to mammals, and even in some bacteria and viruses. The derivatives such as Spisulosine, Clavaminols, Xestoaminols etc. exhibit cytotoxic activity against several different cancer cell lines [2], therefore they deserve significant interest in research. These compounds can be isolated from marine organisms such as sponges, algae and tunicates [3-5] or they can be synthetized by a variety of asymmetric syntheses [6]. Their chemical structures include vicinal amino alcoholic moiety, therefore we focused on utilization of asymmetric Henry reaction for their preparation in this work (Fig. 1). The aim of this work was the study of catalytic activity and enantioselectivity of selected highly efficient enantioselective catalysts of Henry reaction used in the preparation of the sphingolipids Clavaminol A and Xestoaminol C. The study includes own catalysts based on copper(II) complexes of imidazolidine-4-one derivatives [7] as well as commercially available enantioselective catalysts (copper(II) complexes of chiral bisoxazolines, sparteine, chiral diamines etc.). We involved also the heterogeneous forms of catalysts, which can be easily recovered and reused [8]. It was found out, that the most efficient catalysts provided corresponding nitroalcohols with enantioselectivity more than 90 % ee. From this point of view, the asymmetric Henry reaction of appropriate aldehyde with nitroethane and subsequent reduction of nitro group can be considered as suitable synthetic methodology for preparation of these biologically active compounds.	Henry reaction; asymmetric; Clavaminol A; Xestoaminol C