A Diels–Alder Macrocyclization Enables an Efficient Asymmetric Synthesis of the Antibacterial Natural Product Abyssomicin C

Abstract

An efficient and highly diastereoselective intramolecular Diels–Alder reaction is the basis of a concise asymmetric synthesis of the potent antibacterial natural product abyssomicin C (see formula). The complexity of the target structure was reduced to three fragments and required two carbonyl addition reactions to achieve key bond formations.