Stereoselective synthesis of an eleganine A core

Autor:	Gints Smits, Ronalds Zemribo
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Indole test Acylation Indole alkaloid Double bond chemistry Stereochemistry Organic Chemistry Single step Stereoselectivity Physical and Theoretical Chemistry Biochemistry Stereocenter
Zdroj:	Organic & Biomolecular Chemistry. 18:4566-4568
ISSN:	1477-0539 1477-0520
DOI:	10.1039/d0ob00939c
Popis:	A synthetic approach towards the core of a structurally unique cytotoxic indole alkaloid eleganine A has been accomplished for the first time. The synthesis features a stereoselective Ireland-Claisen rearrangement as the key step, enabling the installation of 2 stereogenic centers and a stereodefined double bond in a single step. Furthermore, a SnCl4 promoted acylation of the indole C-2 position allows the coupling of a highly functionalized 4-ethylidene proline fragment with the indole part.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::aae93ee96a64a3d32bcde254802488ef https://doi.org/10.1039/d0ob00939c Zobrazit plný text záznamu