A new route for the synthesis of 3-substituted and 8-hydroxy-3-substituted isocoumarins was developed by modified Julia olefination for initial C–C bond formation between aldehydes and benzylic sulfones. Palladium-catalyzed Meinwald rearrangement was used as a key step for the obtainment of ketone intermediates, which – upon base-promoted intramolecular cyclization – afforded the desired isocoumarins. The developed method paves the way to hitherto unknown 3-glycosylisocoumarins, in general, and 3-glucosylisocoumarins, in particular, wherein the glucosyl moiety is attached to the pyrone ring of the isocoumarin framework. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Indrapal Singh Aidhen

Department Of Chemistry

Kasireddy Sudarshan

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

European Journal of Organic Chemistry

A new strategy for the synthesis of 3-arylisocoumarins and 8-hydroxy-3-arylisocoumarins was investigated by using acyl anion chemistry for the initial C-C bond formation. The obtained keto esters and keto lactones as intermediates underwent based-promoted intramolecular cyclization to afford 3-arylisocoumarins in good yields. The developed methodology was applied for the synthesis of the important natural products thunberginol A and cajanolactone A. © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Synthesis of 3-arylisocoumarins by using acyl anion chemistry and synthesis of thunberginol A and cajanolactone A

The synthesis of (+)-varitriol (1) analogues was achieved through, the use of Julia olefination. The potential anticancer properties of 1 coupled with, our interest in developing building blocks that enable olefin formation under the Julia protocol constitute the basis of our research project. Efforts are aimed at the synthesis of building blocks 2 and 3 and to explore their use towards the synthesis of (+)-varit:riol analogues. Herein, we would, like to present the synthesis of building block 3 and its ability to react with variety of substituted aromatic-, heterocyclic- and carbohydrate-derived aldehydes to yield alkene 6 in moderate to good yields with E as the major isomer. The successful, coupling of 2 with (furanoside moieties) aldehydes 5k, 5m and 5n in particular and the obtainment of compound 23 reflect the promise associated with the new strategy. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

Synthesis of (+)-varitriol analogues via novel and versatile building blocks based on julia olefination

Bioorganic & Medicinal Chemistry

Discovery of Ipragliflozin (ASP1941): A novel C-glucoside with benzothiophene structure as a potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes mellitus

Journal	Data powered by TypesetEuropean Journal of Organic Chemistry
Publisher	Data powered by TypesetWiley-VCH Verlag
ISSN	1434193X
Open Access	No