Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 17, Pages 7588-7594Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301408j
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation (CFI)
- provincial government of Quebec (FQRNT and CCVC)
- Boehringer Ingelheim (Canada) Ltd.
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An oxidative ipso-rearrangement mediated by a hypervalent iodine reagent that enables rapid generation of a functionalized dienone system containing a quaternary carbon center connected to several sp(2) centers has been developed. The process occurs through transfer of an aryl group from a silyl segment present on the lateral chain. As an illustration of the potential of this transformation, a total synthesis of sceletenone, a small alkaloid, is described.
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