Total Synthesis of the Clavicipitic Acids by an Intramolecular Azide Cycloaddition Strategy

Article abstract of DOI:10.1021/jo00187a002

A straightforward total synthesis approach to the structurally unique ergot derailment products, the clavicipitic acids 1 and 2, is described.The synthetic strategy is based on the formation of the seven-membered nitrogen-containing ring of 1 and 2 through an intramolecular azide cycloaddition process.The cycloaddition strategy, which produces solely the imine product 24, does in some sense mimic the proposed biosynthetic pathway to these acids.