Total Syntheses of Cystobactamids and Structural Confirmation of Cystobactamid 919‐2

The cystobactamids are a family of antibacterial natural products with unprecedented chemical scaffolds that are active against both Gram‐positive and Gram‐negative pathogens. Herein, we describe the first total synthesis of cystobactamid 919‐2 from three fragments. Our convergent synthesis enabled both the confirmation of the correct structure and the determination of the absolute configuration of cystobactamid 919‐2.     

Catalytic Enantioselective Aza‐pinacol Rearrangement

The first catalytic enantioselective asymmetric aza‐pinacol rearrangement is reported. The reactions are catalyzed by a chiral phosphoric acid and proceed via a highly organized transition state involving a cyclic aza‐ortho ‐xylylene intermediate to afford the indoline structures with good to excellent enantioselectivity. The synthetic utility of this method is demonstrated by the asymmetric synthesis of a key intermediate to the natural product minfiensine and the identification of a chiral lead compound to repress antibiotic resistance.