A mild and efficient one-pot method has been developed for the stereoselective synthesis of structurally diverse novel iminosugar C-alkynylglycosides. The generality of this methodology has been demonstrated with a wide variety of amines and copper acetylides. This one-pot method has been exploited in the synthesis of new class of DNA cross-linking agents, polyhydroxy 1-vinyl-tetrahydroindolizine derivatives. © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Sundarababu Baskaran

Department Of Chemistry

Sure Siva Prasad

Crosslinking

Glycosides

stereochemistry

Stereoselectivity

Anticancer

Cross linking agents

Facile synthesis

Iminium

IMINOSUGARS

One-pot method

One-pot synthesis

Stereoselective synthesis

Synthesis (chemical)

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Chemistry - A European Journal

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. © 2018 American Chemical Society.

Journal of Organic Chemistry

One-Pot Synthesis of Structurally Diverse Iminosugar-Based Hybrid Molecules

A facile and convergent approach has been developed for the stereoselective construction of biologically important polyhydroxylated 2-acyl indolizidine framework using aza-Cope rearrangement–Mannich cyclization as a key step. The generality of this methodology is demonstrated with various lactol-tosylates derived from carbohydrates. The presented method provides an easy access to indolizidine- and tetrahydroindolizine-based iminosugar derivatives in good yields. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

A Short and Efficient Synthesis of Iminosugar 2-Acyl Indolizidine

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. This journal is © The Royal Society of Chemistry.

Chemical Communications

A diversity oriented one-pot synthesis of novel iminosugar C-glycosides

A diversity-oriented synthesis is described for functionalized chiral building blocks (i.e., 7, 9, 10, 16, and 17) and the biologically active iminosugar, fucosidase inhibitor (2S,3R,4R,5R)-2-(hydroxymethyl)-5- methylpyrrolidine-3,4-diol (22), starting from common chiral intermediate 1a which is obtained through a regioselective reductive cleavage of a bis(benzylidene) acetal. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

European Journal of Organic Chemistry

Diversity-oriented synthesis of useful chiral building blocks from D-mannitol

A stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid, starting from d-glucose is described. The key step in the overall synthesis is a highly regioselective reductive cleavage of benzylidene acetal 13 leading to hydroxymethyl piperidine derivative 14. © 2009 Elsevier Ltd. All rights reserved.

Tetrahedron Letters

A regioselective reductive cleavage of benzylidene acetal: stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

Cambridge Crystallographic Data Centre (CCDC)

Organic Letters

CuI-Catalyzed C1-Alkynylation of Tetrahydroisoquinolines (THIQs) by A3 Reaction with Tunable Iminium Ions

One-Pot Synthesis of Hydrophobically Modified Iminosugar C-Alkynylglycosides: Facile Synthesis of Polyhydroxy Tetrahydroindolizines

Journal	Data powered by TypesetChemistry - A European Journal
Publisher	Data powered by TypesetWiley-VCH Verlag
ISSN	09476539
Open Access	No