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