Issue 24, 2020

Stereoselective synthesis of an eleganine A core

Abstract

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.

Graphical abstract: Stereoselective synthesis of an eleganine A core

Supplementary files

Article information

Article type
Communication
Submitted
06 Mai 2020
Accepted
03 Jun 2020
First published
04 Jun 2020

Org. Biomol. Chem., 2020,18, 4566-4568

Stereoselective synthesis of an eleganine A core

G. Smits and R. Zemribo, Org. Biomol. Chem., 2020, 18, 4566 DOI: 10.1039/D0OB00939C

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