First total synthesis of JS isoprostane.
A stereoselective Julia-Lythgoe olefination followed by an efficient 1,3-allylic transposition of the C-9 hydroxyl group of compound 13 has allowed the first total synthesis of J(2) isoprostane (1), a recently discovered member of the growing isoprostane family. This elusive compound opens up numerous new avenues for the molecular biology of cyclopentenone prostaglandins which are endowed of intriguing biological effects such as antitumor, antiinflammatory, and antiviral activities. In principle, our approach is flexible enough to allow an easy synthesis of other isoprostanes of the J family following the same methodology.
Zanoni
Giuseppe
G
Department of Organic Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, Italy. gzanoni@unipv.it
Porta
Alessio
A
Castronovo
Francesca
F
Vidari
Giovanni
G
D007202:Indicators and Reagents; D028421:Isoprostanes / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015230:Prostaglandin D2 / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D021241:Spectrometry, Mass, Electrospray Ionization
D007202:Indicators and Reagents; D028421:Isoprostanes; C037112:9-deoxy-delta-9-prostaglandin D2; D015230:Prostaglandin D2