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

Yi-Xian Li; Jun-Zhe Wang; Atsushi Kato; Yuna Shimadate; Maki Kise; Yue-Mei Jia; George W J Fleet; Chu-Yi Yu

doi:10.1039/d1ob01725j

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

Org Biomol Chem. 2021 Nov 10;19(43):9410-9420. doi: 10.1039/d1ob01725j.

Authors

Yi-Xian Li^{1

2}, Jun-Zhe Wang^{1

2}, Atsushi Kato³, Yuna Shimadate³, Maki Kise³, Yue-Mei Jia^{1

2}, George W J Fleet⁴, Chu-Yi Yu^{1

2}

Affiliations

¹ 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. yucy@iccas.ac.cn.
² University of Chinese Academy of Sciences, Beijing 100049, China.
³ Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan. kato@med.u-toyama.ac.jp.
⁴ Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.

PMID: 34668913
DOI: 10.1039/d1ob01725j

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.

Publication types

Research Support, Non-U.S. Gov't