WS9326B (<b>1</b>) is a cycloheptadepsipeptide isolated from <i>Streptomyces</i> sp. SNM55 and is distinguished by its rare (<i>Z</i>)-pentenyl cinnamic acid side chain and notable antiangiogenic activity. Herein, we report its total synthesis through a bioispired macrolactonization strategy. Sequential amide couplings followed by Shiina esterification delivered WS9326B in 13 longest linear steps. This bioinspired synthesis provides a versatile platform for producing WS9326B and offers a distinctive perspective on macrocyclization strategy in complex cyclodepsipeptide synthesis, thereby facilitating future biological and medicinal investigations.