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Synthesis of Bridged Cyclopentane Derivatives by Catalytic Decarbonylative Cycloaddition of Cyclobutanones and Olefins.

ABSTRACT: Herein, we report an intramolecular rhodium-catalyzed decarbonylative coupling between cyclobutanones and alkenes that proceeds by C-C activation and provides a distinct approach to a diverse range of saturated bridged cyclopentane derivatives. In this reaction, cyclobutanones serve as cyclopropane surrogates, reacting in a formal (4+2-1) transformation. To demonstrate the efficacy of this method, it was applied in a concise synthesis of the antifungal drug Tolciclate.

SUBMITTER: Zhou X

PROVIDER: S-EPMC5214575 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Synthesis of Bridged Cyclopentane Derivatives by Catalytic Decarbonylative Cycloaddition of Cyclobutanones and Olefins.

Zhou Xuan X Ko Haye Min HM Dong Guangbin G

Angewandte Chemie (International ed. in English) 20161006 44

Herein, we report an intramolecular rhodium-catalyzed decarbonylative coupling between cyclobutanones and alkenes that proceeds by C-C activation and provides a distinct approach to a diverse range of saturated bridged cyclopentane derivatives. In this reaction, cyclobutanones serve as cyclopropane surrogates, reacting in a formal (4+2-1) transformation. To demonstrate the efficacy of this method, it was applied in a concise synthesis of the antifungal drug Tolciclate. ...[more]

PMID: 27712025

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