SYNTHESIS OF (+, -) ZOAPATANOL: SYNTHESIS OF IONOPHORE ANTIBIOTIC X-14547A, COUPLING OF RIGHT AND LEFT WINGS, TRANS BUTADIENE FORMATION, AND 2-KETOPYRROLE FORMATION. N-PHENYLSELENO PHTHALIMIDE (N-PSP) AND N-PHENYLSELENO SUCCINIMIDE (N-PSS), TWO VERSATILE

The total synthesis of ((+OR-)) zoapatanol a novel oxepane diterpene having contragestational properties originally isolated from zoapatanol leaves (Montanoa Tomentosa) by Levine and co-workers of Ortho Pharmaceuticals has been completed in a stereoselective manner. This synthesis allows for significant quantities of pure synthetic ((+OR-)) zoapatanol for biological screening as a mixture of inseparable diastereomers due to the (alpha)-methyl of a carbonyl.;Two novel carriers of the Phenylseleno N-Phenylselenophthalimide (N-PSP) and N-Phenylselenosuccinimide (N-PSS) have been explored for use as reagents in organic synthesis. The preparation of N-PSP is described by a simple and high yield procedure from phenylselenylchloride and potassiumphthalimide. The reactions of N-PSP and N-PSS with olefins containing internal and external nucleophiles to form cyclic substrates and (beta)-hydroxy Phenylselenides respectively is demonstrated. The synthesis of cyclic diphenylseleno ethers from dienes and phenylselenomacrolactones from long chain olefinic acids is detailed using N-PSP or N-PSS. The combination of N-PSP and tributylphosphine for the synthesis of alkyl phenylselenides from alcohols and phenylselenol esters from acids is shown in a high yield process. These reagents are suitable candidates for transformations involved in natural products synthesis since the phenylseleno group can be removed via oxidative elimination or reductive cleavage.;The total synthesis of Ionophore Antibiotic X-14547A, discovered by Westley of Hoffman LaRoche, has been accomplished in a enantioselective manner. This thesis describes the coupling of the two key fragments, the stereospecific formation of the trans-butadiene system, and the introduction of the ketopyrrole system. From this synthesis, two novel derivatives of X-14547A have also been prepared. The biological significance of X-14547A stems from its antibiotic, antitumor, and ruminent feed improvement activity.