Format

Send to

Choose Destination
Chem Sci. 2018 Jan 31;9(9):2432-2436. doi: 10.1039/c8sc00234g. eCollection 2018 Mar 7.

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

Author information

1
Department of Chemistry , University of Pennsylvania , 231 S. 34th St. Philadelphia , PA 19104-6323 , USA . Email: mjoullie@sas.upenn.edu.

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.

Supplemental Content

Full text links

Icon for Royal Society of Chemistry Icon for PubMed Central
Loading ...
Support Center