Issue 9, 2018

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
15 jan 2018
Accepted
31 jan 2018
First published
31 jan 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 2432-2436

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

J. Lee and Madeleine M. Joullié, Chem. Sci., 2018, 9, 2432 DOI: 10.1039/C8SC00234G

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