Issue 43, 2021
From the journal:

Organic & Biomolecular Chemistry

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

Yi-Xian Li,ab   Jun-Zhe Wang,ab   Atsushi Kato, ORCID logo *c   Yuna Shimadate,c   Maki Kise,c   Yue-Mei Jia,ab   George W. J. Fleetd  and  Chu-Yi Yu ORCID logo *ab  

* Corresponding authors

a Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
E-mail: yucy@iccas.ac.cn

b University of Chinese Academy of Sciences, Beijing 100049, China

c Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
E-mail: kato@med.u-toyama.ac.jp

d Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK

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

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Article information

DOI
https://doi.org/10.1039/D1OB01725J
Article type
Paper
Submitted
02 Sep 2021
Accepted
10 Oct 2021
First published
12 Oct 2021

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

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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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