Total Synthesis of (+)-Mutilin: A Transannular [2+2] Cycloaddition/Fragmentation Approach
Han Chen, Zesheng Li, Peng Shao, Haosen Yuan, Si‐Cong Chen, Tuoping Luo
Abstract
A new and enantioselective total synthesis of the diterpenoid (+)-mutilin is described. Following a Claisen rearrangement approach to construct the 6,9-bicycle, a transannular [2+2] photocycloaddition and the ensuing ring-opening reaction were implemented to forge the characteristic 5-6-8 propellane-like skeleton. Subsequent late-stage alkylations and reduction completed the synthesis.
Topics & Concepts
ChemistryPropellaneCycloadditionEnantioselective synthesisTotal synthesisStereochemistryFragmentation (computing)Carbon skeletonClaisen rearrangementSkeleton (computer programming)Ring (chemistry)Bicyclic moleculeMedicinal chemistryOrganic chemistryCatalysisComputer scienceProgramming languageOperating systemPharmacological Effects of Natural CompoundsNatural product bioactivities and synthesisBioactive Compounds and Antitumor Agents