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Issue 13, 2017
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Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids

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Abstract

We present an effective deacylative alkylation strategy for the construction of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position. A wide variety of products with quaternary centers could be accessed by employing simple Pd(0) catalysis under mild reaction conditions. Importantly, the same strategy works equally well for the dimeric 2-oxindole system, furnishing products with a vicinal quaternary center in favour of meso-isomer as the major product. Eventual application to the total syntheses of meso-chimonanthine and meso-folicanthine very well demonstrates the synthetic potential of this strategy.

Graphical abstract: Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids

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Publication details

The article was received on 25 Dec 2016, accepted on 18 Jan 2017 and first published on 19 Jan 2017


Article type: Communication
DOI: 10.1039/C6CC10228J
Citation: Chem. Commun., 2017,53, 2170-2173
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    Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids

    N. Kumar, M. K. Das, S. Ghosh and A. Bisai, Chem. Commun., 2017, 53, 2170
    DOI: 10.1039/C6CC10228J

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