1. Studies directed toward the synthesis of 20B-carbachaparrinone analogs via a samarium (II) iodide ring closure of a highly functionalized intermediate. 2. Synthesis of 5-oxo-cyclopent-1-enecarboxylic acid methyl esters via a novel tandem aldol-knoevena |
Posted on:2003-05-12 | Degree:Ph.D | Type:Thesis |
University:Indiana University | Candidate:DeSelms, Robert Herschel | Full Text:PDF |
GTID:2461390011984082 | Subject:Chemistry |
Abstract/Summary: | |
1. A synthetic approach to analogs of the quassinoid chaparrinone possessing an all carbon E ring is described. Several noteworthy reactions are described, culminating with a samarium (II) iodide promoted Barbier coupling to form the all carbon E ring.; 2. The development of novel synthetic methodology is a prime motivating force in organic synthesis. A synthetic approach to the novel B ring functionality of the sequoiatones is described. The reaction involves a one-pot tandem Aldol-Knoevenagel condensation and is applicable to a variety of substrates.; 3. Novel applications for 5.0 M lithium perchlorate-diethyl ether continue to be discovered. A novel six-membered ring forming reaction involving the enol trapping of an allyl cation is described. Additionally, the reactivity of 3-(hepta-4,6-dienyl)-cycloalk-2-enones under a variety of conditions is described. |
Keywords/Search Tags: | Ring, Described, Novel, Synthesis |
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