Omega chain methylated analogs of PGF2 alpha and PGE2.
Our previously published prostaglandin (PG) synthesis route, in which the omega-chain is added in the penultimate step, provides facile access to a wide variety of omega-chain variant PG analogs. Each series requires only the synthesis of the appropriate methylated acylphosphonate for the Emmons' condensation. The syntheses of analogs bearing the following methylation patterns are detailed: 15-Me; 17,17-(Me) 2; 17, 17, 20-(Me) 3; 18, 18, 20-(Me) 3; 15, 18, 18, 20-(Me) 4; and 15-OMe-18, 18, 20- (Me) 3. The well-known 16., 16-dimethyl prostaglandins have also been prepared by this sequence. The synthesis of 16, 16-tetramethylene-PG analogs is also described.
D008722:Methods; D008745:Methylation; D011459:Prostaglandins E, Synthetic / Q000138:chemical synthesis*; D011461:Prostaglandins F, Synthetic / Q000138:chemical synthesis*; D013237:Stereoisomerism
D011459:Prostaglandins E, Synthetic; D011461:Prostaglandins F, Synthetic