Total Synthesis of (±)-Phomoidride D.
Joyce C LeungAaron A BedermannJón T NjardarsonDavid A SpiegelGraham K MurphyNaoto HamaBarry M TwenterPing DongTatsuya ShirahataIvar M McDonaldMunenori InoueNobuaki TaniguchiTravis C McMahonChristopher M SchneiderNancy TaoBrian M StoltzJohn L WoodPublished in: Angewandte Chemie (International ed. in English) (2018)
Described herein is a synthetic strategy for the total synthesis of (±)-phomoidride D. This highly efficient and stereoselective approach provides rapid assembly of the carbocyclic core by way of a tandem phenolic oxidation/intramolecular Diels-Alder cycloaddition. A subsequent SmI2 -mediated cyclization cascade delivers an isotwistane intermediate poised for a Wharton fragmentation that unveils the requisite bicyclo[4.3.1]decene skeleton and sets the stage for synthesis completion.