Martin, Stephen F.1663534702008-08-282008-08-282007http://hdl.handle.net/2152/3026textAn iminium ion cascade sequence was designed and its implementation attempted to form the pentacyclic core structure of the natural product condylocarpine. Trapping of the transient Pictet-Spengler-type spiroindolenium ion with a latent nucleophile would form two of the five rings of condylocarpine in a regioselective manner. Progress towards the first fully stereocontrolled synthesis of a lysergic acid derivative has been described. The route utilizes intermediates with the appropriate oxidation state for the target, and the two stereocenters are installed via asymmetric catalysis. The d ring and second stereocenter were simultaneously formed via an unprecedented microwave heated asymmetric ring closing metathesis (ARCM).electronicengCopyright is held by the author. Presentation of this material on the Libraries' web site by University Libraries, The University of Texas at Austin was made possible under a limited license grant from the author who has retained all copyrights in the works.CondylocarpineThesis