Synthesis of the sialidase inhibitor siastatin B.
[structure] The resolved piperidinecarboxylate (R)-7 was converted to siastatin B (1) by an efficient and stereoselective sequence that includes a bromo-beta-lactonization and an N-acyliminium azidation. Two analogues (3 and 4) of siastatin were also prepared.
Knapp
S
S
Department of Chemistry; Rutgers-The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854-8087, USA. knapp@rutchem.rutgers.edu
Zhao
D
D
D001386:Azides / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D001386:Azides; D004791:Enzyme Inhibitors; D007783:Lactones; D010880:Piperidines; C011353:siastatin; D009439:Neuraminidase