Chemospecific deuteration of prostaglandin silyl ethers

Complete chemical selectivity (i.e., chemospecificity) has been achieved in the homogeneous deuteration of C5-C6 and endocyclic C10-C11 prostaglandin double bonds without arrangement or partial reduction of C13-C14- or C8-C12 double bonds. The homogeneous deuteration reaction utilizes protection of the C13-C14 double bond as the C15O-silyl ether and protection of the carboxyl group as the methyl ester prior to reduction under molecular deuterium with tris(triphenylphosphine)chlorohodium (I) (Wilkinson's catalyst) in 60:40 acetone:benzene at 25 degrees C. The reaction has been used to prepare six specifically deuterated prostaglandin: 5,6-dideuterio-PGE1 alpha 5,6-dideuterio-PGE1, 5,6-dideuterio-PGB1, 3,3,4,4,5,6-hexadeuterio-PGF1 alpha, 5,6,10,11-tetradeuterio-11-deoxy-PGE1, and 10, 11-dideuterio-11-deoxy-PGE1.