Regiocontrolled intramolecular cyclizations of carboxylic acids to carbon-carbon triple bonds promoted by acid or base catalyst

Masanobu Uchiyama, Hiroki Ozawa, Kazuya Takuma, Yotaro Matsumoto, Mitsuhiro Yonehara, Kou Hiroya, Takao Sakamoto

Research output: Contribution to journalArticlepeer-review

157 Citations (Scopus)

Abstract

We systematically investigated, for the first time, the relationship between regioselectivity and acid/base effects in the cyclization reactions between carboxylic acids and carbon-carbon triple bonds. We found novel acid- and base-promoted cyclizations to selectively give isocoumarin or pyran-2(2H)-one and phthalide or furan-2(5H)-one skeletons, respectively, and established a catalytic version of regioselective heterocyclic ring synthesis. Density functional theory calculations and application to a short route to thunberginol A were also described.

Original languageEnglish
Pages (from-to)5517-5520
Number of pages4
JournalOrganic letters
Volume8
Issue number24
DOIs
Publication statusPublished - 2006 Nov 23
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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