Collect. Czech. Chem. Commun. 1994, 59, 138-148

Synthetic Analogues of Prostaglandins F and E2

Václav Kozmík and Jaroslav Paleček

Institute of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic


The synthesis of new derivatives of prostaglandins F and E2 XIIa,b - XVa,b and XXa,b - XXIIIa,b containing the furan or thiophene nucleus in the upper chain has been accomplished starting from [3aα,4α,5β,6aα]-(±)-hexahydro-5-hydroxy-4-((E)-(3α)-hydroxy-1-octenyl)-2H-cyclopenta[b]furan-2-one (Ia) and [3aα,4α,5β,6aα]-(±)-hexahydro-5-hydroxy-4-[4-(3-chlorophenoxy)-(3α)-hydroxy-1-butenyl]cyclopenta[b]furan-2-one (Ib). The diols Ia and Ib have been converted into the above-mentioned analogues of prostaglandins F and E2 by protecting the hydroxyl groups, subsequent reduction and Wittig reaction with the ylides prepared from the phosphonium salts IV - VII, and final deprotection (or oxidation plus deprotection).