Issue 43, 2021

Stereocomplementary synthesis of casuarine and its 6-epi-, 7-epi-, and 6,7-diepi-stereoisomers

Abstract

Four diastereomers belonging to the family of casuarines, including casuarine (1), 6-epi-casuarine (2), 7-epi-casuarine (13) and 6,7-diepi-casuarine (14), have been synthesized from D-arabinose-derived cyclic nitrone 7 and nitrone-derived aldehyde 4 by a stereocomplementary strategy. Glycosidase inhibition comparison showed that 6-epi-casuarine (2) exhibits enhanced inhibition of trehalase (IC50 = 9.7 μM) and 6,7-diepi-casuarine (14) leads to specific inhibition of trehalase.

Graphical abstract: Stereocomplementary synthesis of casuarine and its 6-epi-, 7-epi-, and 6,7-diepi-stereoisomers

Supplementary files

Article information

Article type
Paper
Submitted
02 Sept. 2021
Accepted
10 Okt. 2021
First published
12 Okt. 2021

Org. Biomol. Chem., 2021,19, 9410-9420

Stereocomplementary synthesis of casuarine and its 6-epi-, 7-epi-, and 6,7-diepi-stereoisomers

Y. Li, J. Wang, A. Kato, Y. Shimadate, M. Kise, Y. Jia, G. W. J. Fleet and C. Yu, Org. Biomol. Chem., 2021, 19, 9410 DOI: 10.1039/D1OB01725J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements