Theses and Dissertations at Montana State University (MSU)
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Item Studies of nucleophile ring opening of oxabicyclic systems in highly polar media : application to a total synthesis of antitumor agent, (-)-epothilone B(Montana State University - Bozeman, College of Letters & Science, 2006) Diep, Nhut Kiet; Chairperson, Graduate Committee: Paul GriecoPolyketides constitute an important family of natural products, having a broad spectrum of biological activity such as antitumor, antibiotic, antifungal, or immunomodulatory action.¹ Many of these compounds possess polypropionates (units with alternating hydroxyl and methyl groups), reflecting their common biosynthesis that is found within nature. Their structural complexity and importance of these compounds as therapeutical agents have made them attractive targets for synthetic organic chemists.¹ Excellent chiral propionate reagents have been developed over the years, including many chiral auxiliaries to direct and promote stereoselectivity, but most recent, investigations have focused upon developing metal-catalyzed asymmetric ring opening. To achieve these results, transition metals (Ni, Pd, Pt) have been employed leading to synthetically useful transformations.