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Practical Route to Neokotalanol and Its Natural Analogues: Sulfonium Sugars with Antidiabetic Activities
Author(s) -
Huang Yuhao,
Gao Yunlong,
He Weigang,
Wang Zihao,
Li Wei,
Lin Aijun,
Xu Jinyi,
Tanabe Genzoh,
Muraoka Osamu,
Wu Xiaoming,
Xie Weijia
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201900761
Subject(s) - sulfonium , chemistry , moiety , intramolecular force , nucleophile , stereochemistry , thiol , intermolecular force , combinatorial chemistry , nucleophilic substitution , coupling reaction , salt (chemistry) , organic chemistry , molecule , catalysis
Abstract An efficient and divergent approach toward the synthesis of all four de‐O‐sulfonated sulfonium type α‐glucosidase inhibitors, originally isolated from plants of genus Salacia , is reported for the first time. The key strategy features a coupling reaction between thiol derivatives and a diiodide counterpart. The newly designed thiol coupling partner presents high chemical stability, while the diiodide partner could be easily obtained with increased overall yields compared with conventional routes. The intermolecular nucleophilic substitution reaction followed by a diastereoselective intramolecular cyclization provided the target five‐member sulfonium salt structure, which was connected in an α‐orientation to a polyhydroxylated side‐chain moiety.