The specific aim of this work is the development of synthetic strategy and methodology for the total synthesis of tirandamycin, streptolydigin and Bu2313--all representatives of the 3-acyltetramic acid antibiotic class. Previous work has resulted in the synthesis of tirandamycic acid, and knowledge gained in this effort will be applied to the synthesis of the antibiotics themselves. The synthetic work entails two major phases--one concerned with the 3,9-dioxabicyclo(3.3.1)nonane ring system construction and the other, the synthesis of appropriate tetramic acid derivatives that can effectively be joined to the dioxabicyclic ring structure. The approach used for the former syntheses entails carbohydrate precursors and utilizes the power of the Claisen rearrangement for the stereocontrolled synthesis. A new and novel modification of the Calisen sequence is proposed. The latter phase involves the generation of Wittig reagents from appropriate tetramic acid derivatives such that the union between these protions and the bicyclic ring sections may be accomplished through a Wittig condensation.