A biomimetic approach to the synthesis of an antiviral marine steroidal orthoester.
Orthoesterol B, a marine natural product exhibiting antiviral activities, contains a [3.2.1]-bicyclic orthobutyrate bridging the steroid side chain and ring D. A biosynthetic reaction was proposed by which rearrangement of an epoxy ester results in the formation of the orthoester moiety. Steroidal model compounds incorporating 16-butyroxy and 20,22-epoxy groups were synthesized from tigogenin and were shown to rearrange to orthoesters under mild acidic catalysis.
Giner
José-Luis
JL
Department of Chemistry, SUNY-ESF, Syracuse, NY 13210, USA. jlginer@syr.edu
Faraldos
Juan A
JA
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002776:Cholestanes / Q000737:chemistry; D002855:Chromatography, Thin Layer; D017934:Coronavirus / Q000187:drug effects; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis; D005256:Leukemia Virus, Feline / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D018716:Molecular Mimicry; D015394:Molecular Structure; D009975:Orthomyxoviridae / Q000187:drug effects; D011161:Porifera / Q000737:chemistry; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
D000998:Antiviral Agents; D002776:Cholestanes; D004852:Epoxy Compounds; D013256:Steroids; C462723:orthoesterol B