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Approaches to the total synthesis of (+/-)-pseudomonic acids. Model studies and reagent development in stereo- and regiocontrolled Pd-catalyzed alkylations and arylations of allylic alcohol derivatives

Posted on:1998-04-18Degree:Ph.DType:Thesis
University:University of Maryland, College ParkCandidate:Brescia, Marc-RaleighFull Text:PDF
GTID:2461390014476146Subject:Chemistry
Abstract/Summary:
The formal total synthesis of ;In conjunction with the synthesis of the "core" pyran unit of pseudomonic acid, regio- and stereocontrolled reduction and alkylation of ketals was also examined. Reduction of bicyclic ketals afforded highly functionalized cis- or trans-substituted dihydropyrans. The stereochemical outcome of the reduction was dependent on the combination of reagents utilized. The resulting pyrans are precursors to polyether toxins and antibiotics. Alkylation of ketals, using allyltrimethylsilanes, afforded pyrans suitable for our Pd(0)-catalyzed methodology and resulted in a second formal total synthesis of pseudomonic acid A.
Keywords/Search Tags:Total synthesis
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