Synthesis and Biological Evaluation of the Southern Hemisphere of Spirastrellolide A and Analogues
作者:Jagadeesh Nagendra Manda、Barry B. Butler、Aaron Aponick
DOI:10.1021/acs.joc.0c01867
日期:2020.11.6
The synthesis and biologicalevaluation of truncated spirastrellolide A analogues comprised of the southern hemisphere against protein phosphatase 2A are described. A convergent synthesis was designed featuring two gold-catalyzed cyclization reactions, specifically, a dehydrative cyclization of monoallylic diols for the synthesis of the tetrahydropyran (A-ring) and a regioselective spiroketalization
Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers
作者:Guanghao Huang、Régis Guillot、Cyrille Kouklovsky、Boris Maryasin、Aurélien de la Torre
DOI:10.1002/anie.202208185
日期:2022.10.17
The inverse-electron-demand Diels–Alder cycloaddition between 2-pyrones and acyclic enolethers was investigated. Bridged bicyclic lactones were obtained diastereo- and enantioselectively and converted into synthetically relevant polysubstituted enantioenriched cyclohexene and cyclohexadiene derivatives. Mechanistic evidence as well as DFT calculations point towards a stepwise mechanism.