A mild and highly efficient one-pot method has been developed for the stereoselective synthesis of structurally diverse novel iminosugar C-aryl glycosides. The generality of this methodology is demonstrated with a wide variety of aryl nucleophiles and amines. The synthetic potential of this methodology is further shown in the domino synthesis of iminosugar based hybrid molecules.
A simple and efficient method for the stereoselective synthesis of isoxazoline/isoxazole-fused iminosugar derivatives has been developed using intramolecular nitrile oxide cycloaddition (INOC) as a key step. Iminosugar C-nitromethyl glycosides, derived from simple carbohydrates, served as excellent nitrile oxide precursors in 1,3-dipolar cycloaddition reactions. N-Alkenyl iminosugar C-nitromethyl glycosides afforded novel isoxazoline-fused indolizidine-, pyrrolizidine-, and quinolizidine-based iminosugars in excellent yields with a high degree of stereoselectivity, whereas N-alkynyl iminosugar C-nitromethyl glycosides furnished the corresponding isoxazole containing tricyclic iminosugars in very good yields.
Described herein is a novel one-pot, three-component reaction where aldehydes, electron-rich arenes, and TMSCN in the presence of BF3-OEt2 allowed direct access to a number of diarylacetonitriles under mild reaction conditions in good to excellent yields.
A new type of three-component reaction was developed consisting of aldehydes, electron-rich (hetero)arenes, and trialkyl phosphite, which provided facile access to a wide range of diarylmethylphosphonates under mild reaction conditions. Simple one-or two-step synthetic manipulation of the resulting compounds enabled us to reach several polycyclic (hetero)aromatic systems efficiently.
A one-pot iminium-ion-based strategy has been developed for the synthesis of structurally novel iminosugar-based hybrid molecules. Iminium ion derived from l-rhamnose lactol-mesylate reacted with electron-rich aromatic systems in an inter/intra molecular fashion to furnish pyrrolidine-based iminosugar C-aryl glycosides with a high degree of stereoselectivity. Iminium ion also reacted readily with active methylene compounds such as 4-hydroxycoumarin, 4-hydroxyquinolinone, and lawsone to provide iminosugar C-coumarin/quinolinone/naphthoquinonyl glycosides in very good yields. Azomethine ylide generated from an iminium ion derivative underwent dipolar cycloaddition reaction with 1,4-quinones to furnish novel isopyrrolonaphtho/anthroquinon-based iminosugar-hybrids. The preliminary cytotoxic activities of some of the synthesized iminosugar-hybrids have been assayed against various human cancer cell lines and some of the hybrid molecules exhibited promising anticancer activities.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.