An efficient and divergent approacht owardt he synthesis of all four de-O-sulfonated sulfonium type aglucosidase inhibitors,o riginally isolated from plants of genus Salacia, is reported for the first time.T he key strategy features ac oupling reaction between thiol derivatives and ad iiodide counterpart. The newly designed thiol coupling partner presents high chemical stability,w hile the diiodide partner could be easily obtained with increased overall yields compared with conventional routes.T he intermolecular nucleophilic substitution reaction followed by adiastereoselective intramolecular cyclization provided the target fivemember sulfonium salt structure,w hich was connected in an a-orientation to ap olyhydroxylated side-chain moiety.
An efficient and divergent approacht owardt he synthesis of all four de-O-sulfonated sulfonium type aglucosidase inhibitors,o riginally isolated from plants of genus Salacia, is reported for the first time.T he key strategy features ac oupling reaction between thiol derivatives and ad iiodide counterpart. The newly designed thiol coupling partner presents high chemical stability,w hile the diiodide partner could be easily obtained with increased overall yields compared with conventional routes.T he intermolecular nucleophilic substitution reaction followed by adiastereoselective intramolecular cyclization provided the target fivemember sulfonium salt structure,w hich was connected in an a-orientation to ap olyhydroxylated side-chain moiety.
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