Synthesis of a sulfonium ion analogue of the glycosidase inhibitor swainsonine.
The synthesis of a bicyclic sulfonium ion analogue of a naturally occurring indolizidine alkaloid, swainsonine, in which the bridgehead nitrogen atom is replaced by a sulfonium ion, has been achieved by a multistep synthesis starting from (2S,3S,4R)-2,3-dibenzyloxy-4-formaldehyde-thiolane. The synthetic strategy relies on the intramolecular displacement of a leaving group on a pendant acyclic chain by a cyclic thioether. This bicyclic sulfonium salt provides a candidate with which to further probe the hypothesis that a sulfonium salt carrying a permanent positive charge would be an effective glycosidase inhibitor.
Kumar
Nag S
NS
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6.
Pinto
B Mario
BM
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D007477:Ions / Q000737:chemistry; D015394:Molecular Structure; D013452:Sulfonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017026:Swainsonine / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
D004791:Enzyme Inhibitors; D007477:Ions; D013452:Sulfonium Compounds; D006026:Glycoside Hydrolases; D017026:Swainsonine