Intramolecular α-amidoalkylation of an olefin for the synthesis of a useful prostaglandin intermediate

Article abstract of DOI:10.1021/jo00314a024

The α,β-unsaturated aldehyde 1 is an important intermediate in the preparation of a number of prostaglandins such as prostaglandin C₂ and thromboxane B₂.A method was developed by starting with the ene lactone 3 and using an intramolecular α-amidoalkylation reaction as the key step that made available this useful molecule in six operations.Formation of the lactam 15, as well as its final conversion to the target aldehyde 1, will be discussed.