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  • Title: Total synthesis of the tropoloisoquinoline alkaloid pareitropone via alkynyliodonium salt chemistry and related studies.
    Author: Feldman KS, Cutarelli TD, Di Florio R.
    Journal: J Org Chem; 2002 Nov 29; 67(24):8528-37. PubMed ID: 12444635.
    Abstract:
    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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