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 Sep 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

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