A Divergent Asymmetric Total Synthesis of Coprophilin and Four Trichodermic Acids via a [1,5]-Hydride Shift–Aldol Cascade

The asymmetric syntheses of coprophilin and four members of the trichodermic acid family of natural products are disclosed. Our work employs a number of key transformations, including an aluminum-promoted [1,5]-hydride shift–aldol cascade reaction, an exo-selective Diels–Alder cycloaddition, and a late-stage Fleming–Tamao oxidation. These key steps efficiently construct the bicyclic core of the natural products, which can then be readily functionalized in a divergent manner, allowing the synthesis of a wide range of natural product targets.