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Total synthesis of the reported structure of ceanothine D via a novel macrocyclization strategy

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Abstract

The first total synthesis of the reported structure of ceanothine D, a cyclopeptide alkaloid found in red root, was achieved using a highly convergent synthetic strategy. Highlights of the synthesis include the first concomitant macrocyclization and formation of the unique chiral tertiary alkyl-aryl ether bond with complete regio- and stereo-control in the presence of a sensitive Z-enamide moiety to access the strained para-cyclophane present in its structure. This synthetic strategy may be broadly applicable in the generation of other structurally similar cyclopeptide alkaloids, enabling further biological and chemical investigations.

Graphical abstract: Total synthesis of the reported structure of ceanothine D via a novel macrocyclization strategy

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Publication details

The article was received on 15 Jan 2018, accepted on 31 Jan 2018 and first published on 31 Jan 2018


Article type: Edge Article
DOI: 10.1039/C8SC00234G
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    Total synthesis of the reported structure of ceanothine D via a novel macrocyclization strategy

    J. Lee and Madeleine M. Joullié, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C8SC00234G

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