Stereoselective Synthesis of Baulamycin A

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Abstract
New structural classes of antibiotics are rare, structurally-novel broad-spectrum antibiotics exceptionally so. The recently discovered baulamycins constitute a remarkable example of these highly-prized compounds and, as such, have attracted considerable attention in the form of both synthetic efforts and biological studies. For the first time, we report a gram-scale preparation of the common carbon framework of the baulamycin family, as well as the total synthesis of its most potent member, baulamycin A. Our approach employs highly-stereoselective, catalyst-controlled asymmetric conjugate additions to thioesters to set key stereocenters, as well as the first reported use of “dry ozonolysis” to reveal a masked carboxylic acid in the total synthesis of a natural product.
Funding Information
  • National Institutes of Health (CA070375, R35 GM118101)

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