Abstract
Studies on the synthesis of isocarbacyclin [9 (O) -methano-Δ6 (9a) -prostaglandin I1], a stable prostacyclin analogue, were carried out starting from bicyclic synthons which were prepared from a chiral 4-hydroxy-2-cyclopentenone via three-component coupling process. We elabolated several methodologies, which involved regioselective or regiospecific alkylation reactions by use of various transition metal catalysts : (1) regioselective alkylation of bicyclic allylic alcohol synthons with alkyllithium in the presence of copper (I) salt and aminophosphonium salt, (2) regiospecific alkylation of bicyclic carbonate synthons with bissulfone derivative in the presence of palladium catalyst, and (3) regioselective alkylation of bicyclic phosphate synthons with zinccopper reagent. In addition, several deuterium- or tritium-labeled isocarbacyclin derivatives were also synthesized by the use of these methodologies.
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