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New methodologies for the synthesis of natural products

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Gentiopicroside (GPS), a bitter secoiridoid glycoside, is an important constituent present in many gentianaceous plants and these plants have been widely used as traditional herbal remedies for the treatment of digestion dysfunctions, chronic and acute dysentery, liver disease, fungal and bacterial infection etc.
Since GPS is the major component of such plants, it attracts the scientist’s attention to study its biological activity in vivo and vitro experiments. From these experiments, it has been revealed that it exhibited choleretic, antihepatotoxic, anti-inflammatory, and analgesic properties.

We studied a possible approach toward Gentiopicroside based on an organocatalyzed [3+3] type reaction between an unsaturated aldehyde and the enol form of a,b-acyl ester.

Associated ref : Studies towards the synthesis of secoiridoids. S. Wu, Y. Zhang, J. Agarwal, E. Mathieu, S. Thorimbert, L. Dechoux Tetrahedron, 2015, 71, 7663‑7669.

This work open the door for the use of Methyl coumalate as a convenient and very reactive electrophile that react with Grignard reagents to deliver stereoselectively dienoic acids.

Associated ref : Stereoselective synthesis of conjugated α-Z,γ-E – and α-Z,γ -Z dienoic acids. Kinetic torquoselectivity versus thermodynamic control. J. Agarwal, O. Bayounes, S. Thorimbert, L. Dechoux RSC Advances 2014, 2272-2275

We are still exploring the underexplored reactivity of Methyl Coumalate.