82933-76-4Relevant academic research and scientific papers
Synthesis of Six-Membered-Ring Analogues of 6α-Carba-PGI2
Sih, John C.
, p. 4311 - 4315 (1982)
To further develop our understanding of prostacyclin (PGI2, 1) structure-activity relationships, we have prepared the six-membered-ring analogues of 6α-Carba-PGI2 (carbacyclin, 3).An intramolecular alkylation of 1,3-dithiane was utilized as the critical reaction for securing the key cyclohexanone intermediate 8.The carboxyl side chains were attached to 8 by using conventional Wittig chemistry.Acid removal of the tetrahydropyranyl protective groups and separation of the resulting E and Z isomers afforded the 7a-homo-6α-Carba-PGI2 analogues 6 and 7.The reactions described are simple to perform and useful for preparetive purposes.The six-membered-ring carbacyclins reported were found to be much less active than parent carbacyclin in inhibiting human platelet aggregation.
