A --> J prostaglandin swap: a new tactic for cyclopentenone prostaglandin synthesis.
A practical methodology for the synthesis of J-type prostaglandins has been developed starting from the well-consolidated approaches established for the synthesis of A-type prostaglandins. An efficient 1,3-allylic transposition of the C-9 hydroxyl group of intermediate 4 furnished the advanced precursor 5 for J(2) synthesis. Our optimized A-J swap protocol employed selenium chemistry, involving the [2,3] sigmatropic rearrangement of secondary allylic selenoxide 11a.
Zanoni
Giuseppe
G
Dipartimento di Chimica Organica, Università di Pavia, Via Taramelli 10, 27100 Pavia, Italy. gzanoni@unipv.itgzanoni@unipv.it
Castronovo
Francesca
F
Perani
Eleonora
E
Vidari
Giovanni
G
D007202:Indicators and Reagents; D008958:Models, Molecular; D015230:Prostaglandin D2 / Q000031:analogs & derivatives* / Q000737:chemistry*; D011453:Prostaglandins / Q000138:chemical synthesis / Q000737:chemistry*; D011454:Prostaglandins A / Q000737:chemistry*
D007202:Indicators and Reagents; D011453:Prostaglandins; D011454:Prostaglandins A; C037112:9-deoxy-delta-9-prostaglandin D2; D015230:Prostaglandin D2