<p>Direct carbon&mdashcarbon bond formation via soft enolization and in situ enolate formation provides a straightforward approach to certain key transformations of synthetic organic chemistry. Reactions are generally operationally simple and proceed under mild conditions using untreated, reagent&ndashgrade solvent open to the air. Using this direct approach as a basis, we have developed methods for the synthesis of β&ndashhydroxy thioesters, β&ndashketo thioesters, and 1,3&ndashdiketones, which are key intermediates for the synthesis of natural products, pharmaceuticals, and other biologically relevant compounds. In particular, we describe: 1) a direct aldol addition of simple thioesters, 2) a direct synthesis of 1,3&ndashdiketone compounds, 3) a direct crossed&ndashClaisen reaction, and 4) an <italic>anti<italic>&ndashselective four&ndashcomponent direct aldol cascade reaction.</p><p>Progress toward the total synthesis of apratoxin D is described. The key steps of the synthesis involve the asymmetric alkylation via chiral <italic>N<italic>&ndashamino cyclic carbamate (ACC) hydrazones, a new technology recently developed in our group.</p> / Dissertation
| Identifer | oai:union.ndltd.org:DUKE/oai:dukespace.lib.duke.edu:10161/1170 |
| Date | January 2009 |
| Creators | Zhou, Guoqiang |
| Contributors | Coltart, Don M. |
| Source Sets | Duke University |
| Language | en_US |
| Detected Language | English |
| Type | Dissertation |
| Format | 1354858 bytes, application/pdf |
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