The purpose of this project is to explore synthetic methods which may be used to prepare compounds containing macrocyclic lactone rings. The project is inspired by the naturally occurring antibiotic methymycin, which is a highly substituted twelve membered lactone. There is presently a dearth of methods which may be used to prepare this type of lactone ring. For example, direct lactonization of an 11- hydroxy carboxylic acid fails. In this phase of the project, we wish to explore a possible route which we call the "sulfur template approach" to medium rings in general, and to lactones in particular. We wish to perfect the synthetic method, learn something of the chemistry of the proposed intermediate bi- and tri-cyclic sulfonium salts, and perhaps apply such an approach to the synthesis of the fungal anti-metabolic curvularin.
NIH ExPorter
NIH ExPorter