Total Synthesis of Kavaratamides A–C and Unnatural Analogs

Marine cyanobacteria are a rich source of structurally diverse compounds with biological activity. Herein, we report the total synthesis of kavaratamide A (<b>1</b>), a bioactive lipodepsipeptide isolated from <i>Moorena bouillonii</i>. The total synthesis of <b>1</b> required 16 steps, with a longest linear sequence of 9 steps, and an overall yield of 2.9%. Our convergent synthetic approach led to the efficient synthesis of kavaratamide A-C, C25-<i>epi-</i>kavaratamide A, and deoxy-kavaratamide A from a common intermediate providing a blueprint for facilitating rapid structure-activity relationship (SAR) studies.