Development of New Reactions for Synthesis of Cyclopentanoids and their Application

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4-Cyclopentene-1,3-diol monoacetate (1) is an attractive compound for synthesis of cyclopentanoids. However, the use along this line had been limited due to lack of efficient reactions for installation of carbon nucleophiles onto the ring. Herein, we have developed new reactions based on RMgX and Cu(I) for S_N2 and anti S_N2' reactions, thus producing 4-substituted 2-cyclopenten-1-ols (1,4-isomers) or 2-substituted 3-cyclopenten-1-ols (1,2-isomers) depending on the ratio of RMgZ/Cu(I) and solvent used. In addition, we developed reagents and conditions for attaching second carbon nucleophiles to the 1,4-isomers produced above. We applied these reactions to synthesis of 12-oxo-PDA, OPC-8:0, OPC-8:0, and Δ^<12>-PGJ_2.