PART I. NEW ORGANOSELENIUM METHODOLOGY. PART II. STUDIES DIRECTED TOWARD THE TOTAL SYNTHESIS OF THE NATURAL PRODUCT FORSKOLIN (ELECTROCYCLIZATION, CYCLOADDITION, SELENOETHER)

Part I. The preparation and reactivity of alpha-selenofurans and alpha-selenopyrans have been studied. These substrates underwent oxidative elimination to give cyclic enol ethers, alkylation at the anomeric position, or nucleophilic addition/rearrangement at the selenium atom. The synthesis of cyclic alpha-alkylselenenyl ketones afforded a substrate which was alkylated at the two-position upon base treatment and subsequent electrophile introduction. The mechanism of these alkylations was studied extensively.;Part II. Both intermolecular Diels-Alder and six pi electrocyclization methodology were employed in the synthesis of bicyclic, highly-functionalized forskolin intermediates. Further elaboration and stereochemical manipulation of these intermediates provided attractive strategy for the natural product's synthesis.