The foci of this research are threefold. First, the intramolecular addition of nitrile oxides to alkenes will be used as an entry to the synthesis of phomactin A and cornutin A. Second, epoxides will be transformed into cyclopropanes and the methodology applied to the preparation of the unusual Streptomyces metabolites FR-900,848 and U-106,305. Third, synthetic routes to compounds of the nonadride family of natural products will be explored. With this renewal award, the Synthetic Organic Program is supporting the research of Dr. James D. White of the Department of Chemistry at Oregon State University. Professor White will focus his work on developing total synthetic approaches to several natural products that possess interesting biochemical properties.