917249-21-9Relevant articles and documents
Regiocontrolled intramolecular cyclizations of carboxylic acids to carbon-carbon triple bonds promoted by acid or base catalyst
Uchiyama, Masanobu,Ozawa, Hiroki,Takuma, Kazuya,Matsumoto, Yotaro,Yonehara, Mitsuhiro,Hiroya, Kou,Sakamoto, Takao
, p. 5517 - 5520 (2007/10/03)
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.