Date of Award
2015-01-01
Degree Name
Doctor of Philosophy
Department
Chemistry
Advisor(s)
Shizue Mito
Abstract
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.
Language
en
Provenance
Received from ProQuest
Copyright Date
2015
File Size
84 pages
File Format
application/pdf
Rights Holder
Sudhakar Kalagara
Recommended Citation
Kalagara, Sudhakar, "Total SynThesis of Syringolides 1 and 2" (2015). Open Access Theses & Dissertations. 1079.
https://scholarworks.utep.edu/open_etd/1079