Gram-Scale Enantioselective Synthesis of (+)-Lucidumone
Guanghao Huang, Cyrille Kouklovsky, Aurélien de la Torre
Abstract
The first enantioselective total synthesis of (+)-lucidumone is described through a 13-step synthetic pathway (longest linear sequence). The key steps involve the formation of a bridged bicyclic lactone by an enantioselective inverse-electron-demand Diels-Alder cycloaddition, C-O bond formation to assemble two fragments, and a one-pot retro-[4 + 2]/[4 + 2] cycloaddition cascade. The synthesis is scalable, and more than one gram of natural product was synthesized in one batch.
Topics & Concepts
ChemistryEnantioselective synthesisGramScale (ratio)Organic chemistryCombinatorial chemistryStereochemistryCatalysisBacteriaPhysicsBiologyQuantum mechanicsGeneticsAdvanced Synthetic Organic ChemistryChemical synthesis and alkaloidsAlkaloids: synthesis and pharmacology