Journal
TETRAHEDRON LETTERS
Volume 55, Issue 30, Pages 4248-4250Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.05.054
Keywords
Akolactone A; Aldol reaction; Autoxidation; Boron enolate; Lactone
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Department of Education of Quebec (FQRNT program)
- FQRNT Centre in Green Chemistry and Catalysis (CGCC)
- CGCC for a doctoral scholarship
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A simple, bioinspired synthesis of the naturally occurring Cdc25B inhibitor paracaseolide A is reported. Key steps include: (i) an aerobic oxidation of a 2-silyloxyfuran to the corresponding silyl ketoester, and (ii) the preparation of the former intermediate by silylation of an alpha-alkylidenebutenolide. Both of these high-yielding transformations are unprecedented. (C) 2014 Elsevier Ltd. All rights reserved.
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