The aims of the proposed project are: one, to develop chiral Gamma-alkoxyallyl boronates which may be used in the synthesis of carbohydrates and related materials; two, to explore the stereochemical outcome of the condensation of Delta substituted allyl boronates with aldehydes as a prelude to the synthesis of the antibiotic tetrin A; three, to examine the Diels-Alder chemistry of butadienyl boronates as a route to cyclic allyl boronates. These may then be elaborated further into a variety of carbocyclic skeletons; four, to carry out the total synthesis of the polyene antibiotic tetrin A. The synthesis will establish the stereochemistry of tetrin A and provide the methodology for the synthesis and structure proof of the other related tetraenes, pimaricin, lucensomycin, tetrin B and arenomycin. A knowledge of the stereochemical relationships in these substances is important when trying to establish structure activity relationships for the purpose of developing new chemotherapeutic agents.
