Show simple item record

Methods for Direct Carbon-Carbon Bond Formation and Their Application to Natural Product Synthesis

dc.contributor.advisor Coltart, Don M.
dc.contributor.author Zhou, Guoqiang
dc.date.accessioned 2009-05-01T18:34:35Z
dc.date.available 2011-07-26T04:30:04Z
dc.date.issued 2009
dc.identifier.uri https://hdl.handle.net/10161/1170
dc.description.abstract <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>
dc.format.extent 1354858 bytes
dc.format.mimetype application/pdf
dc.language.iso en_US
dc.subject Chemistry, Organic
dc.title Methods for Direct Carbon-Carbon Bond Formation and Their Application to Natural Product Synthesis
dc.type Dissertation
dc.department Chemistry
duke.embargo.months 24


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record