First enantioselective total synthesis of (8S,12R,15S)-prostaglandin J(2).
Enantioselective synthesis of natural PGJ(2) has been accomplished for the first time starting from the commercially available enantiopure aldehyde 7 in 10% overall yield. The key reaction was a novel prostaglandin class interconversion, i.e., an allylic 1,3-transposition across alcohol 9 derived from compound 14 in 73% overall yield. In principle, the unnatural enantiomer of PGJ(2) could be obtained starting from the commercially available enantiopure monobenzoate 7a following our strategy.
Zanoni
Giuseppe
G
Dipartimento di Chimica Organica, Università di Pavia, Via Taramelli 10, 27100 Pavia, Italy. gzanoni@unipv.it
Porta
Alessio
A
De Toma
Quintino
Q
Castronovo
Francesca
F
Vidari
Giovanni
G
D000447:Aldehydes / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015230:Prostaglandin D2 / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D007202:Indicators and Reagents; C037112:9-deoxy-delta-9-prostaglandin D2; D015230:Prostaglandin D2