Issue 5, 2019

Enantioselective synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters: application to the total synthesis of (+)-alexine

Abstract

A straightforward synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters from the corresponding racemic α-amino-β-keto esters by using a ATH/DKR protocol has been developed. This method gives moderate to excellent yields with high chemo-, diastereo- and enantioselectivities for a broad range of substrates. In order to highlight the versatility of the methodology it was applied in an efficient asymmetric synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-alexine.

Graphical abstract: Enantioselective synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters: application to the total synthesis of (+)-alexine

Supplementary files

Article information

Article type
Paper
Submitted
08 Jan 2019
Accepted
12 Jan 2019
First published
21 Jan 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 2799-2802

Enantioselective synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters: application to the total synthesis of (+)-alexine

L. Yu and P. Somfai, RSC Adv., 2019, 9, 2799 DOI: 10.1039/C9RA00173E

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