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Synthesis of an Intein-mediated Artificial Protein Hydrogel
Published on: January 27, 2014
Total Synthesis of Okeaniamide A
Sanju Bhaskar1, Rajib Kumar Goswami1
1School of Chemical Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.
Abstract:
The stereoselective total synthesis of okeaniamide A, a marine lipopeptide with therapeutic potential against diabetes mellitus and obesity, has been disclosed for the first time. The salient synthetic features include Negishi reaction, Kumada coupling, Julia-Kocienski olefination, and Crimmins acetate aldol reaction. Extension of the polyketide segment to the full molecular framework was achieved through consecutive peptide coupling, followed by late-stage oxidation at position C2. Okeaniamide A was found to be sensitive to C3 epimerization, particularly under oxidative and mildly acidic conditions.
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