A Diels–Alder Macrocyclization Enables an Efficient Asymmetric Synthesis of the Antibacterial Natural Product Abyssomicin C†
This work was supported by Princeton University, a Bristol‐Myers Squibb unrestricted research grant in synthetic organic chemistry (E.J.S.), the National Institute of General Medical Sciences (GM065483), Merck Research Laboratories (E.J.S.), a NRSA fellowship (1 F32 GM070235) from the National Institutes of Health (USA; B.A.H.), and a National Science Foundation (USA) Predoctoral Fellowship (C.D.). We thank Prof. Robert Pascal, Jr. for the conformational analysis of compound 5 and Dr. István Pelczer for assistance with the NMR spectroscopic analysis.
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.
