Stereoselective synthesis of pseudopeptide microbial agent AI-77-B.
[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.
Ghosh
A K
AK
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA. arunghos@uic.edu
Bischoff
A
A
Cappiello
J
J
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
D000900:Anti-Bacterial Agents; D000897:Anti-Ulcer Agents; D003374:Coumarins; D049934:Isocoumarins; D010455:Peptides; C039360:AI 77B