title: Stereoselective synthesis of pseudopeptide microbial agent AI-77-B.
abstract: [structure: see text]. An efficient and highly stereoselective synthesis of the gastroprotective natural product AI-77-B is described. The stereocenters of the hydroxy amino acid moiety were generated by an ester-derived titanium-enolate-mediated syn-aldol reaction, a Curtius rearrangement, and application of Dondoni's aldehyde homologation. Condensation with the dihydroisocoumarin fragment and subsequent deprotecting transformations furnished optically active AI-77-B.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA. arunghos@uic.edu
authors.forename: A K
authors.initials: AK
authors.lastname: Ghosh
authors.forename: A
authors.initials: A
authors.lastname: Bischoff
authors.forename: J
authors.initials: J
authors.lastname: Cappiello
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000897:Anti-Ulcer Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D049934:Isocoumarins; D010455:Peptides; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D000897:Anti-Ulcer Agents; D003374:Coumarins; D049934:Isocoumarins; D010455:Peptides; C039360:AI 77B