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]
Dubost, C., Marko, I., & Ryckmans, T. (2006). A concise total synthesis of the lichen macrolide (+)-aspicilin. Organic Letters, 8(22), 5137-5140. https://doi.org/10.1021/ol0620287 (Original work published 2006)