Synthesis of two bioactive natural products: FR252921 and pseudotrienic acid B.
Concise and highly convergent syntheses of the immunosuppressive agent FR252921 and the related antimicrobial natural product pseudotrienic acid B were achieved from a common intermediate by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereo- and regioselective cross-metathesis to generate the triene moieties, and a Stille cross-coupling to install the dienic units.
Amans
Dominique
D
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris, France.
Bellosta
Véronique
V
Cossy
Janine
J
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry; D002384:Catalysis; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry
D000890:Anti-Infective Agents; D001688:Biological Products; C474178:FR 252921; D007166:Immunosuppressive Agents; D007769:Lactams; D007783:Lactones; D018942:Macrolides; C505309:pseudotrienic acid B; D014025:Titanium