Out of options? Even though a systematic approach was chosen, which led to a set of four diastereomeric macrolides modeled around the proposed structure of leiodolide B (see picture), the puzzle concerning the stereostructure of this cytotoxic metabolite derived from a deep‐sea sponge still remains unsolved.

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The total synthesis of the polyhydroxylated macrolide (+)-aspicilin 5 is described using as a key step a highly diastereoselective allylation of aldehyde 6 with the uniquely functionalized allylstannane 1. (+)-Aspicilin is obtained in 18 steps and 10% overall yield. [structure: see text]