Total synthesis of the reported structure of ceanothine D
| Autor: | Jisun, Lee, Madeleine M, Joullié |
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| Rok vydání: | 2018 |
| Předmět: | |
| Zdroj: | Chemical Science |
| ISSN: | 2041-6520 |
| Popis: | A novel regio- and stereocontrolled macrocyclization strategy was developed for the first synthesis of ceanothine D. 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. |
| Databáze: | OpenAIRE |
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