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Total synthesis of aristolactam alkaloids via synergistic C-H bond activation and dehydro-Diels-Alder reactions.

ABSTRACT: A concise total synthesis of aristolactam alkaloids by a synergistic combination of C-H bond activation and dehydro-Diels-Alder reactions is described. To achieve the synthesis two new synthetic methodologies, namely the oxidative cyclization of benzamides with vinyl sulfone leading to 3-methyleneisoindolin-1-ones via a ruthenium-catalyzed C-H bond activation, and a dehydro-Diels-Alder reaction followed by the fluoride ion mediated desulfonylation of 3-methyleneisoindolin-1-ones with benzynes, were developed. The method presented allows the opportunity for the construction of all the rings of aristolactams from easily available starting materials.

SUBMITTER: Reddy MC

PROVIDER: S-EPMC6100235 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Total synthesis of aristolactam alkaloids <i>via</i> synergistic C-H bond activation and dehydro-Diels-Alder reactions.

Reddy Mallu Chenna MC Jeganmohan Masilamani M

Chemical science 20170323 5

A concise total synthesis of aristolactam alkaloids by a synergistic combination of C-H bond activation and dehydro-Diels-Alder reactions is described. To achieve the synthesis two new synthetic methodologies, namely the oxidative cyclization of benzamides with vinyl sulfone leading to 3-methyleneisoindolin-1-ones <i>via</i> a ruthenium-catalyzed C-H bond activation, and a dehydro-Diels-Alder reaction followed by the fluoride ion mediated desulfonylation of 3-methyleneisoindolin-1-ones with benz ...[more]

PMID: 30155216

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