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Issue 47, 2018
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Total synthesis of the potent anti-inflammatory natural product solomonamide A along with structural revision and biological activity evaluation

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Abstract

Herein, we report the total synthesis of solomonamide A along with its structural revision for the first time. The natural product possesses very potent anti-inflammatory activity, and it contains a macrocyclic peptide having four consecutive stereocenters on an unnatural amino acid component. The key features in the present synthesis include the application of an Evans aldol reaction, ligand-free Heck macrocyclization and chemoselective oxidations. The challenging task of fixing the stereochemistry of OH at the C5-position was accomplished with the help of DFT calculations, applying a quantum-mechanical (QM)/NMR combined approach. Biological evaluation in a mouse paw edema model revealed that a low dose (0.3 mg kg−1) of the synthesized solomonamide A showed 74% reduction at 6 h, which was comparable to a high dose (10 mg kg−1) standard drug dexamethasone effect (75% at 6 h). Thus, we further confirmed the revised structure of solomonamide A.

Graphical abstract: Total synthesis of the potent anti-inflammatory natural product solomonamide A along with structural revision and biological activity evaluation

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Publication details

The article was received on 01 Nov 2018, accepted on 15 Nov 2018 and first published on 16 Nov 2018


Article type: Communication
DOI: 10.1039/C8OB02713G
Citation: Org. Biomol. Chem., 2018,16, 9138-9142
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    Total synthesis of the potent anti-inflammatory natural product solomonamide A along with structural revision and biological activity evaluation

    G. R. Jachak, P. R. Athawale, H. Agarwal, M. K. Barthwal, G. Lauro, G. Bifulco and D. S. Reddy, Org. Biomol. Chem., 2018, 16, 9138
    DOI: 10.1039/C8OB02713G

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