Organic synthesis with tricarbonyliron lactone complexes

Abstract

π-Ally tricarbonyliron lactone complexes are useful precursors for organic synthesis. These stable complexes are readily prepared from a variety of organic substrates and may be respectively converted to β- and δ-lactones by selective oxidation or exhaustive carbonylation. The natural products massoialactone, parasorbic acid, the carpenter bee pheromone and malyngolide were prepared by using the iron carbonyl methodology, along with precursors for the ionophore antibiotic CP 61405 and avermectin B1a synthesis. Several corresponding lactam complexes were obtained by treatm ent of the π-allytricarbonyliron lactones with amines in the presence of Lewis acids. These complexes were used in the formal total synthesis of the nocardicins and ( + )-thienamycin.