A new functionalised sulphone-based building block has been synthesised that enabled C-C bond formation through Julia olefination. The utility of developed building block was demonstrated by successful synthesis of two natural products lunularic acid, hydrangeic acid and initial libraries of their analogues. © 2017 Informa UK Limited, trading as Taylor & Francis Group.

Indrapal Singh Aidhen

Department Of Chemistry

Ramesh Mukkamala

HYDRANGEIC ACID

HYDRANGEIC ACID DERIVATIVE

LUNULARIC ACID

LUNULARIC ACID DERIVATIVE

natural product

sulfone derivative

unclassified drug

salicylic acid derivative

stilbene derivative

sulfone

article

chemical bond

chemical structure

drug synthesis

Olefination

Salicylates

Stilbenes

Sulfones

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

Valuable building block for the synthesis of lunularic acid, hydrangeic acid and their analogues.

Natural Product Research

A common building block for the synthesis of amorfrutin and cajaninstilbene acid derivatives has been developed. The library of synthesized compounds has enabled identification of new nontoxic ligands of peroxisome proliferator-activated receptors (PPAR) and potential inhibitors of the transcriptional corepressor protein NCoR. The biological data holds promise in identification of new potential leads for the antidiabetic drug discovery process. © 2014 American Chemical Society.

Fulltext

Organic Letters

A common building block for the syntheses of amorfrutin and cajaninstilbene acid libraries toward efficient binding with peroxisome proliferator-activated receptors

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.

European Journal of Organic Chemistry

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

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Tetrahedron

Titanocene(III) chloride mediated radical-induced synthesis of 3,4-dihydroisocoumarins: synthesis of (±)-hydrangenol, (±)-phyllodulcin, (±)-macrophyllol and (±)-thunberginol G

Efficient syntheses of (±)-hydrangenol, (±)-phyllodulcin and (±)-macrophyllol

Valuable building block for the synthesis of lunularic acid, hydrangeic acid and their analogues

Journal	Data powered by TypesetNatural Product Research
Publisher	Data powered by TypesetTaylor and Francis Ltd.
ISSN	14786419
Open Access	No