Total Synthesis of Prostaglandin F2α via Nickel-Promoted Stereoselective Cyclization of 1,3-Diene and Aldehyde

Article abstract of DOI:10.1055/s-1997-3268

The total synthesis of prostaglandin F_2α (PGF_2α) was accomplished via nickel-promoted cyclization of 1,3-diene and aldehyde in a chain in the presence of 1,3-cyclohexadiene (1,3-CHD). The cyclization of 16 prepared in an optically active form from chiral epoxy alcohol 10 stereoselectively gave the key intermediate 18, which has both an α-chain and the four contiguous chiral carbon centers in PGF_2α, in a one-pot reaction. Intermediate 18 was successfully transformed into PGF_2α.