Total synthesis of the tropoloisoquinoline alkaloid pareitropone via alkynyliodonium salt chemistry and related studies

Ken S. Feldman, Timothy D. Cutarelli, Romina Di Florio

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)8528-8537
Number of pages10
JournalJournal of Organic Chemistry
Volume67
Issue number24
DOIs
StatePublished - Nov 29 2002

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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