Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 6, Pages 1933-1936Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409464
Keywords
antibiotics; cross coupling; natural products; stereoselective synthesis
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Funding
- Latsis Prize
- Novartis
- Swiss National Science Foundation as part of the NCCR Molecular Systems Engineering
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Fidaxomicin, also known as tiacumicinB or lipiarmycinA3, is a novel macrocyclic antibiotic that is used in hospitals for the treatment of Clostridium difficile infections. This natural product has also been shown to have excellent bactericidal activity against multidrug-resistant Mycobacterium tuberculosis. In spite of its attractive biological activity, no total synthesis has been reported to date. The enantioselective synthesis of the central 18-membered macrolactone is reported herein. The key reactions include ring-closing metathesis between a terminal olefin and a dienoate moiety for macrocyclization, a vinylogous Mukaiyama aldol reaction, and a Stille coupling reaction of sterically demanding substrates. The retrosynthesis involves three medium-sized fragments, thus leading to a flexible yet convergent synthetic route.
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