Total synthesis of angelone enabled by a remarkable biomimetic sequence

摘要

The natural product angelone was readily accessed with a remarkable biomimetic journey that sequentially features carbonyl formation-elimination, 6π-electrocyclization, visible light-promoted singlet O _2 Diels-Alder reaction, Kornblum-DeLaMare-type peroxide rearrangement, 6π-electrocyclic ring-opening, and conjugative addition-elimination as the key steps. With key intermediates isolated and characterized, this study stands to reveal a rare system in which bio-inspired synthetic strategies were found to mirror experimental realities.