New Total Synthesis and Structure Confirmation of Putative (+)-hyacinthacine C and (+)-5--hyacinthacine C

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 2

PMID 35496868

Authors

Livia Dikosova

Barbora Otockova

Tomas Malatinsky

Jana Dohanosova

Maria Kopacova

Anna durinova

Lucie Smutna

Frantisek Trejtnar

Robert Fischer

Affiliations

Soon will be listed here.

Abstract

A unique synthesis of polyhydroxylated pyrrolizidine alkaloids, namely (+)-hyacinthacine C and (+)-5--hyacinthacine C is presented. The strategy relies on a 1,3-dipolar cycloaddition of an l-mannose derived nitrone, which owing to its great -stereoselectivity builds up the majority of the required stereocenters. The following key steps include Wittig olefination and iodine-mediated aminocyclisation, that provide two epimeric pyrrolizidines with the appropriate configuration. As a result, structure and steric arrangement of the first synthetically prepared (+)-hyacinthacine C are proved to be correct, clearly confirming the inconsistency with the stereochemistry assigned to the natural sample. With respect to the previously proven glycosidase inhibitory activities, the antiproliferative effect of (+)-hyacinthacine C and (+)-5--hyacinthacine C was evaluated using several cell line models.

Citing Articles

Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation.

durina L, durinova A, Trejtnar F, Janotka L, Messingerova L, Dohanosova J Beilstein J Org Chem. 2021; 17:2781-2786.

PMID: 34900008 PMC: 8630432. DOI: 10.3762/bjoc.17.188.

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