Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 25, Pages 7581-7584Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201402323
Keywords
aromatic ring umpolung; hypervalent iodine; natural products; oxidation; total synthesis
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation (CFI)
- provincial government of Quebec (FQRNT)
- provincial government of Quebec (CCVC)
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A convergent and enantioselective synthesis of fortucine was achieved from the starting materials tyrosine methyl ester and 3-hydroxy-4-methoxybenzaldehyde. The synthesis is based on two key steps mediated by a hypervalent iodine reagent. This work has enabled us to reassign the absolute configuration of the natural product reported in the literature.
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