Divergent total syntheses of kavaratamide A, B, and C

Abstract

The stereoselective total synthesis of kavaratamide A, a linear lipodepsipeptide isolated from Moorena bouillonii, a marine cyanobacterium from Kavaratti, India, was successfully achieved using a simple and efficient method. The synthesis strategy uses a Reformatsky reaction to stereoselectively construct the (3S)-3-hydroxydecanoic acid (HDA) fragment, which is a key lipid component of the molecule. The peptide backbone was constructed via sequential Steglich esterification and amidation reactions to ensure high efficiency and selectivity. Furthermore, the total syntheses of kavaratamide B and C were also accomplished using a divergent total synthesis strategy, thereby demonstrating the versatility of this approach. The developed synthetic route provides access to these bioactive natural products in good yields and offers a platform for further medicinal chemistry investigations.