Total synthesis of Syringolides 1 and 2

Sudhakar Kalagara, University of Texas at El Paso


The total synthesis of Syringolides is described. The synthetic pathway was designed in order to synthesize Syringolides in high yields using inexpensive starting materials. The synthesis strategy features a preparation of the linear tricarbonyl compound followed by intramolecular cyclization. The linear precursor is divided into two fragments, β-keto acid and protected D-xylulose, which are the key fragments and were synthesized from α,β-unsaturated compound followed by asymmetric dihydroxylation. The α,β-unsaturated compound was efficiently prepared by a Wittig reaction between aldehyde and ylide fragments. The butenolide derivative was also achieved by the Knoevenagel condensation of the tricarbonyl compound..

Subject Area

Analytical chemistry|Organic chemistry

Recommended Citation

Kalagara, Sudhakar, "Total synthesis of Syringolides 1 and 2" (2015). ETD Collection for University of Texas, El Paso. AAI3708546.