Concise Total Synthesis of (−)‐Vermiculine through a Rhodium‐Catalyzed C2‐Symmetric Dimerization Strategy

A short and efficient synthesis of the C2‐symmetric antibiotic (−)‐vermiculine by utilizing an enantioselective catalytic one‐step dimerization methodology as key‐step to construct the core structure is reported. The late‐stage modifications feature a double metathesis homologation followed by a dou...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-03, Vol.25 (14), p.3532-3535
Main Authors: Steib, Philip, Breit, Bernhard
Format: Article
Language:English
Subjects:
Antibiotics
Catalysis
Chemical synthesis
Chemistry
Dimerization
Enantiomers
Homology
Metathesis
Oxidation
Rhodium
total synthesis
vermiculine
Wacker-type oxidation
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Summary:A short and efficient synthesis of the C2‐symmetric antibiotic (−)‐vermiculine by utilizing an enantioselective catalytic one‐step dimerization methodology as key‐step to construct the core structure is reported. The late‐stage modifications feature a double metathesis homologation followed by a double Wacker‐type oxidation. These key‐steps allowed the synthesis of vermiculine in only seven steps, starting from commercially available building blocks. A short and efficient synthesis of the C2‐symmetric antibiotic (−)‐vermiculine utilizing an enantioselective catalytic one‐step dimerization methodology as key‐step to construct the core structure is reported. This key step allowed the synthesis of vermiculine in only seven steps starting from commercially available building blocks (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201900216