Alkynyliodonium salts in organic synthesis. Application to the total synthesis of the tropoloisoquinoline alkaloid pareitropone

Ken S. Feldman, Timothy D. Cutarelli

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

The synthesis of the tropoloisoquinoline alkaloid pareitropone has been accomplished in 14 steps from 2,3,4-trimethoxybenzoic acid. The key transformations include the generation of an alkylidenecarbene intermediate through intramolecular addition of a tosylamide anion to an alkynyliodonium salt, and the cycloaddition of that carbene to a peri positioned aromatic ring to afford a cycloheptatrienylidene product featuring the intact pareitropone skeleton.

Original languageEnglish (US)
Pages (from-to)11600-11601
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number39
DOIs
StatePublished - Oct 2 2002

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Synthetic Chemistry Techniques
Alkaloids
Cycloaddition
Negative ions
Salts
Acids
Cycloaddition Reaction
Skeleton
Anions
pareitropone
carbene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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Alkynyliodonium salts in organic synthesis. Application to the total synthesis of the tropoloisoquinoline alkaloid pareitropone. / Feldman, Ken S.; Cutarelli, Timothy D.

In: Journal of the American Chemical Society, Vol. 124, No. 39, 02.10.2002, p. 11600-11601.

Research output: Contribution to journalArticle

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