Synthesis of a Tiacumicin B Protected Aglycone

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 tiacu...

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Bibliographic Details
Published in:Organic letters 2017-08, Vol.19 (15), p.4006-4009
Main Authors: Jeanne-Julien, Louis, Masson, Guillaume, Astier, Eloi, Genta-Jouve, Grégory, Servajean, Vincent, Beau, Jean-Marie, Norsikian, Stéphanie, Roulland, Emmanuel
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Catalysis
Chemical Sciences
Copper - chemistry
Drug Design
Fidaxomicin - chemical synthesis
Glycosylation
Molecular Structure
Palladium - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01744