Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 24, Pages 8528-8537Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo026337w
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- NIGMS NIH HHS [GM37681] Funding Source: Medline
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The first chemical synthesis of pareitropone, by a route featuring application of alkynyliodonium salt chemistry, is described. The key transform initiates with addition of an alkylidenecarbene, derived by intramolecular nucleophile addition to the alkynyliodonium moiety, to a proximal aromatic ring. This addition delivers a highly strained norcaradiene substructure that rapidly reorganizes to furnish the pareitropone skeleton.
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