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General synthesis of prostaglandins (PGs) has been accomplished based on a one-pot three-component coupling using a combination of organocopper or organozincate conjugate addition to 4-hydroxy-2-cyclopentenone followed by trapping of resulting enolate with an organic halide. Based on the use of this synthetic methodology, biologically significant PG derivatives including ent-Δ-PGA1, 15SAPNIC ([ H]APNIC), and 15R–TIC have also been synthesized. Ultimately, organozincate conjugate addition combined with the enolate trapping by an organic triflate results in practical green threecomponent coupling comprising the use of stoichiometric amounts of three components (enone, αand ω-side chains in a nearly 1:1:1 ratio) without using HMPA and heavy metals. General methodology for introducing short-lived C and F radionuclides into carbon frameworks has been established by developing rapid C-[C]methylation and C-[F]fluoromethylation using Pd-mediated rapid cross-coupling between [C]methyl iodide and an organotributylstannane or organoboronate; or [F]fluoromethyl bromide and organoboronate, respectively, allowing the synthesis of a wide variety of biologically significant and disease-oriented PET probes such as 15R-[C]TIC. Moreover, Pdmediated rapid C-[C]carbonylation using [C]CO and organoboronate at ambient temperature under atmospheric pressure using conventional helium carrier gas has been explored. Further, C-[C]carboxylation has been promoted using [C]CO2 and organoboronate with Rh catalyst under atmospheric pressure.

Green Process of Three-Component Prostaglandin Synthesis and Rapid <sup>11</sup>C Labelings for Short-Lived PET Tracers