@article {45356,
	title = {Total synthesis of the potent anti-inflammatory natural product solomonamide A along with structural revision and biological activity evaluation},
	journal = {Organic \& Biomolecular Chemistry},
	volume = {16},
	year = {2018},
	month = {DEC},
	pages = {9138-9142},
	type = {Article },
	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.},
	issn = {1477-0520},
	doi = { 10.1039/c8ob02713g},
	author = {Jachak, Gorakhnath R. and Athawale, Paresh R. and Agarwal, Heena and Barthwal, Manoj Kumar and Lauro, Gianluigi and Bifulco, Giuseppe and Reddy, D. Srinivasa}
}
