In 2024, the Fürstner group at MPI published a total synthesis of the norcembranoid Scabrolide B and Sinuscalide C. During their synthesis, they found out a precursor to Sinuscalide C could be converted into Ineleganolide, another complex norcembranoid of great synthetic interest. As a bonus, prolonged exposure to reaction condition also afforded Horiolide in 25% yield, thus synthetically accessing two new unexpected norcembranoid natural products from a single precursor.
Deduce a plausible reaction mechanism for both synthetic transformations. (Hint: classic carbonyl chemistry!)
For reference:
Lin, D. S., Georg Späth, Meng, Z., Lianne, Christophe Farès, and Alois Fürstner. (2024)
“Total Synthesis of the Norcembranoid Scabrolide B and Its Transformation into Sinuscalide C, Ineleganolide, and Horiolide.”
Journal of the American Chemical Society. 146, 35, 24250–24256
doi: 10.1021/jacs.4c09467