Nitro-Olefin Trapping Reactions of Enolates In Situ Generated by Conjugate Addition Reaction: Short Syntheses of PGE1, 6-Oxo-PGE1, 6-Oxo-PGF1α, and PGI2

Article abstract of DOI:10.1016/S0040-4020(01)90018-3

The nitro-olefin trapping of the enolates in situ generated by conjugate addition of organocopper reagents to the chiral oxygenated cyclopentenone synthon, R-4, gives the three-component coupling products in a regiospecific manner.The intermediary nitronate anion 17 is further transformed into the nitro compound or 6-oxo-PGE₁ (19) in a single pot.This coupling reaction is applicable to syntheses of naturally occurring prostaglandins such as PGE₁, 6-oxo-PGF_1α, and PGI₂.