Total Synthesis of the Fungal Metabolite Trienylfuranol A through Nucleophilic Diastereodivergent Additions to Oxocarbenium Ions

Herein, we describe the first total synthesis of trienylfuranol A, a fungal triene-substituted tetrahydrofuran metabolite. The stereoselectivity chiral center bearing trienyl side chain was diastereodivergently controlled by addition nucleophilic species on substituted ?-butyrolactone. Remarkably, C-nucleophilic or hydride onto oxocarbenium intermediate leads to opposite diastereoselectivity reported for Kishi Woerpel models. use Hantzsch ester (HEH) as organic donor has enabled us obtain desired stereochemistry. A achieved in 8 steps from acetaldehyde and pyruvic acid.