Regiocontrolled Intramolecular Cyclizations of Carboxylic Acids to Carbon−Carbon Triple Bonds Promoted by Acid or Base Catalyst

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)...

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Bibliographic Details
Published in:Organic letters 2006-11, Vol.8 (24), p.5517-5520
Main Authors: Uchiyama, Masanobu, Ozawa, Hiroki, Takuma, Kazuya, Matsumoto, Yotaro, Yonehara, Mitsuhiro, Hiroya, Kou, Sakamoto, Takao
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Carboxylic Acids - chemical synthesis
Catalysis
Cyclization
Furans - chemical synthesis
Heterocyclic Compounds - chemical synthesis
Hydrangea - chemistry
Isocoumarins - chemical synthesis
Pyrans - chemical synthesis
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062190+