Omega chain methylated analogs of PGF2 alpha and PGE2

• Published in: Prostaglandins Vol. 22; no. 5; p. 809
• Main Authors: Andersen, N H, Subramanian, N, Imamoto, S, Picker, D H, Ladner, D W, McCrae, D A, Lin, B S, De, B
• Format: Journal Article
• Language: English
• Published: United States 01-11-1981
• Subjects: Methods; Methylation; Prostaglandins E, Synthetic - chemical synthesis; Prostaglandins F, Synthetic - chemical synthesis; Stereoisomerism
• ISSN: 0090-6980
• DOI: 10.1016/0090-6980(81)90220-3

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.