The chemistry of N-aminoaziridines as chiral auxiliaries in hydrazone alkylations and other reactions will be thoroughly explored. The chemistry should allow the preparation of 1,3-skipped polymethylated carbon chains in a highly convergent and enantioselective manner. Extensions to Shapiro-type elimination reactions promise to result in efficient new methods of chiral alkene construction. The methodology will be applied to the synthesis of the macrolactone antibiotic venturicin. %%% With this award, the Organic Synthesis Program will support the research of Dr. A. Richard Chamberlin at the Unversity of California-Irvine. The research explores the development of chiral methodologies for synthesis of the important polyol and polypropionate structures found in important antibiotic families. This should benefit research in biochemistry and medicine, as well as in the chemical industry.
