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Stereoselective Synthesis of Baulamycin A.

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.

SUBMITTER: Thielman JR

PROVIDER: S-EPMC7271067 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Stereoselective Synthesis of Baulamycin A.

Thielman Jonathan R JR Sherman David H DH Williams Robert M RM

The Journal of organic chemistry 20200207 5

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, bau ...[more]

PMID: 31970985

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