Stereoselective synthesis of the cytotoxic 14-membered macrolide aspergillide A.
A stereoselective synthesis of the cytotoxic 14-membered macrolide aspergillide A has been performed. The preparation of a cis-2,6-disubstituted tetrahydropyran ring via stereoselective reduction of an intermediate cyclic hemiacetal was one key feature of the synthesis. The macrocyclic lactone ring was created by means of a ring-closing metathesis (RCM), whereby the new C=C bond displayed exclusively the undesired Z configuration. Conversion to the required E configuration was achieved via photochemical isomerization.
Díaz-Oltra
Santiago
S
Departamento de Química Inorgánica y Orgánica, Universitat Jaume I, E-12071 Castellón, Spain.
Angulo-Pachón
César A
CA
Murga
Juan
J
Carda
Miguel
M
Marco
J Alberto
JA
D000900:Anti-Bacterial Agents; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008027:Light; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010777:Photochemistry; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D007783:Lactones; D018942:Macrolides; C526623:aspergillide A