title: A --> J prostaglandin swap: a new tactic for cyclopentenone prostaglandin synthesis.
abstract: 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.
authors.affiliation: Dipartimento di Chimica Organica, Università di Pavia, Via Taramelli 10, 27100 Pavia, Italy. gzanoni@unipv.itgzanoni@unipv.it
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Zanoni
authors.forename: Francesca
authors.initials: F
authors.lastname: Castronovo
authors.forename: Eleonora
authors.initials: E
authors.lastname: Perani
authors.forename: Giovanni
authors.initials: G
authors.lastname: Vidari
mesh_terms: 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*
chemical_list: D007202:Indicators and Reagents; D011453:Prostaglandins; D011454:Prostaglandins A; C037112:9-deoxy-delta-9-prostaglandin D2; D015230:Prostaglandin D2