decarboxylative alkenylation with vinyl iodide 39 to deliver 40 in 62% yield, which upon exposure to AcOH afforded the natural product 5 (67% yield). This intuitive approach to the construction of 5 is a striking departure from prior art (Figure ) and to polyketide synthesis in general. The overall strategy outlined for 5 could be employed seven more times for the divergent total syntheses of solistatine (41), verbalactone (42), avocadene (43), gingerdiol (44), streptenol B (45), exserolide (46), and PF1163A (47) resulting in reduced step-counts and improved ideality (Figure ). Notably, all previous routes to these natural products rely exclusively on polar-bond disconnections (see SI for the full detail and references).