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Concise Total Synthesis of (−)‐Vermiculine through a Rhodium‐Catalyzed C 2 ‐Symmetric Dimerization Strategy
Author(s) -
Steib Philip,
Breit Bernhard
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900216
Subject(s) - enantioselective synthesis , rhodium , metathesis , combinatorial chemistry , catalysis , total synthesis , stereochemistry , chemistry , organic chemistry , polymerization , polymer
A short and efficient synthesis of the C 2 ‐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.