Issue 50, 2021

New total synthesis and structure confirmation of putative (+)-hyacinthacine C3 and (+)-5-epi-hyacinthacine C3

Abstract

A unique synthesis of polyhydroxylated pyrrolizidine alkaloids, namely (+)-hyacinthacine C3 and (+)-5-epi-hyacinthacine C3 is presented. The strategy relies on a 1,3-dipolar cycloaddition of an L-mannose derived nitrone, which owing to its great syn-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 C3 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 C3 and (+)-5-epi-hyacinthacine C3 was evaluated using several cell line models.

Graphical abstract: New total synthesis and structure confirmation of putative (+)-hyacinthacine C3 and (+)-5-epi-hyacinthacine C3

Supplementary files

Article information

Article type
Paper
Submitted
17 Aug 2021
Accepted
10 Sep 2021
First published
24 Sep 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 31621-31630

New total synthesis and structure confirmation of putative (+)-hyacinthacine C3 and (+)-5-epi-hyacinthacine C3

L. Dikošová, B. Otočková, T. Malatinský, J. Doháňošová, M. Kopáčová, A. Ďurinová, L. Smutná, F. Trejtnar and R. Fischer, RSC Adv., 2021, 11, 31621 DOI: 10.1039/D1RA06225E

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