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Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer

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Abstract

Asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer, in an atropisomerically pure form, are described. Chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl propanone and naphthylamine followed by acetylation provided two atropisomerically pure tertiary amides. Subsequent stereospecific Bischler–Napieralski reaction of each of these tertiary amides with triflic anhydride provided ancistrocladinium A or its atropdiastereomer, as a single atropisomer, respectively.

Graphical abstract: Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer

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Publication details

The article was received on 12 Mar 2017, accepted on 31 Mar 2017 and first published on 10 Apr 2017


Article type: Research Article
DOI: 10.1039/C7QO00195A
Citation: Org. Chem. Front., 2017, Advance Article
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    Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer

    K. Kim and C. Cheon, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00195A

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