Optimized and Scalable Synthesis of Carba‐α‐d‐Glucosamine

An efficient, high‐yielding synthesis of carba‐α‐d‐glucosamine is reported. Key features of this optimized route include an innovative protecting group strategy and an unusual, stereoconvergent Ferrier carbocyclization of a hindered substrate. The sequence enables the synthesis of larger amounts of this structurally novel antibiotic to allow more detailed biological evaluations of its unique mode of action. A scalable route to carba‐α‐d‐glucosamine involves a stereoconvergent Ferrier rearrangement of hindered substrates in combination with a uniform protective group strategy and will enable more detailed biological studies of the unique mode of action of this potent novel antibiotic.