||The overall purpose of this project has been to develop an effective inhibitor of Acyl-CoA cholesterol O-acyltransferase (ACAT), based upon the fundamental structure of the phytotoxin, helminthosporol. The specific focus of this author was the desisopropyl analog of the natural product. The proposed synthetic route revolved around the formation of a [3.2.1]-bicyclooctanone core common to the helminthosporols, followed by specific adaptations to afford the desired target. A principal portion of the research has been invested in a development of an effective route towards a construction of the bicyclooctanone core, relying essentially upon a sequence of silyl-directed Nazarov cyclization, a Michael-induced ring closing reaction and divinylcyclopropane rearrangement. Currently two methods have been explored for the Michael addition, a Darzens condensation and a sulfur ylide addition based on work by Trost.