Total synthesis of biologically important amino sugars via thenitroaldol reaction
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2016, TetrahedronCitation Excerpt :Thus obtained synthetically versatile β-nitroalcohols 118 and 119 were afterwards stereoselectively converted to a pyrroloisoquinoline derivative 120 or (+)-Spisulosine, respectively (Scheme 49). Pyrroloisoquinoline ring system forms the central skeleton of the Erythrina alkaloid group.107 ( +)-Spisulosine ES285 was isolated from Spisula polynyma, and has been shown to possess long-lasting antitumor cytotoxic activity on the nanomolar scale, both in vitro and in vivo.108
Synthesis, spectral characterization and crystal structure of Ni(II) pyridoxal thiosemicarbazone complexes and their recyclable catalytic application in the nitroaldol (Henry) reaction in ionic liquid media
2014, PolyhedronCitation Excerpt :Shibasaki reported the first asymmetric version of the nitroaldol reaction in 1992 [33]. Since then various transition metals such as Cu [34], Zn [35], Co [36], Cr [37], Pd [38], Ru [39] and rare metals [40] have been applied to the catalytic version of the nitroaldol reaction. In contrast, nickel, an attractive surrogate for precious metals in terms of its abundance and low cost, has not been investigated so far in the nitroaldol reaction.
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2010, TetrahedronCitation Excerpt :Modified carbohydrates play an important role in the synthesis of antibodies,1 enzymes,2 and biologically active compounds.3 Recently we published the highly stereoselective synthesis of methyl-branched 2-amino-2-deoxy-aldoses from protected sugar aldehydes 1 (Scheme 1).4 Aldehydes 1 are elongated via introduction of the C-1–C-3 unit by homoaldol reaction of enantioenriched homoenolate reagent 2 to deliver enol carbamates 3.5