Convergent, stereoselective syntheses of the glycosidase inhibitors broussonetines D and M.
The first syntheses of the polyhydroxylated alkaloids (iminosugars) broussonetines D and M, glycosidase inhibitors of the pyrrolidine class, have been performed in a convergent, stereocontrolled way from D-serine as the chiral starting material. A cross metathesis step was one key feature of the synthesis. The versatility of the synthetic concept chosen permits the access to many members of this compound family, both natural ones and analogues thereof.
Ribes
Celia
C
Depart. de Q. Inorgánica y Orgánica, Univ. Jaume I, Castellón, E-12071, Castellón, Spain.
Falomir
Eva
E
Murga
Juan
J
Carda
Miguel
M
Alberto Marco
J
J
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D011759:Pyrrolidines; C540208:broussonetine D; C540209:broussonetine M; D006026:Glycoside Hydrolases