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Issue 5, 2017
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Total synthesis of aristolactam alkaloids via synergistic C–H bond activation and dehydro-Diels–Alder reactions

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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.

Graphical abstract: Total synthesis of aristolactam alkaloids via synergistic C–H bond activation and dehydro-Diels–Alder reactions

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Publication details

The article was received on 12 Jan 2017, accepted on 20 Mar 2017 and first published on 23 Mar 2017


Article type: Edge Article
DOI: 10.1039/C7SC00161D
Citation: Chem. Sci., 2017,8, 4130-4135
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    Total synthesis of aristolactam alkaloids via synergistic C–H bond activation and dehydro-Diels–Alder reactions

    M. C. Reddy and M. Jeganmohan, Chem. Sci., 2017, 8, 4130
    DOI: 10.1039/C7SC00161D

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