Tetrahedron
Tetrahedron
4 years ago

First total synthesis of glabramycin B and revision of its relative configuration

First total synthesis of glabramycin B and revision of its relative configuration
Structural revision of glabramycin B, which is an antibacterial 10-membered lactone isolated from a fermentation broth of Neosartorya glabra, was achieved by enantioselective synthesis of our proposed structure. The correct structure of glabramycin B was presumed on comparison with related compounds, and synthesis of it was succeeded via dianion alkylation, Shiina's lactonization and Stille cross-coupling. By this synthesis, we were able to correct the reported structural misassignment, and to confirm the relative configuration of glabramycin B to be 10S*,11S*,15R*,20S*.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017304532

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