4 years ago

Synthesis of a Tiacumicin B Protected Aglycone

Synthesis of a Tiacumicin B Protected Aglycone
Stéphanie Norsikian, Jean-Marie Beau, Vincent Servajean, Emmanuel Roulland, Eloi Astier, Louis Jeanne-Julien, Grégory Genta-Jouve, Guillaume Masson
Tiacumicin B is an antibiotic endowed with the remarkable ability to interact with a new biological target, giving it an inestimable potential in the context of the ever-growing and worrisome appearance of resistances of bacteria and mycobacteria to antibiotics. The synthesis of an aglycone of tiacumicin B ready for glycosylation is reported. The key steps of this approach are a [2,3]-Wittig rearrangement, a Pd/Cu-catalyzed allene–alkyne cross-coupling, a E-selective cross-metathesis, and a final ring-size selective macrolactonization.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01744

DOI: 10.1021/acs.orglett.7b01744

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