Divergent Total Syntheses of 2, 6‐Dioxabicyclo[3.3.1]nonan‐3‐one Styryllactones: (−)‐Goniopypyrone, (+)‐Goniochelienlactone and (+)‐7‐Acetylgoniochelienlactone

Abstract Stereoselective total syntheses of (+)‐goniochelienlactone, (+)‐7‐acetylgoniochelienlactone and (−)‐goniopypyrone were accomplished by divergent strategies starting from readily available chiral pool methyl α ‐D‐mannopyranoside. The present work provided an efficient strategy for the stereoselective construction of highly functionalized dioxabicyclo[3.3.1]nonan‐3‐one ring system through a sequential Bernet‐Vasella‐type reductive elimination/nucleophilic addition and a sequential cross‐metathesis/intramolecular oxa‐Michael addition in a one‐pot process.