Palladium-mediated cyclizations of gamma-oxoallenes: synthesis of structurally modified nucleic acids

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Texas Tech University

The goals of the research described in this dissertation were to study the palladium-mediated intramolecular nucleometallatlon/methoxycarbonylation of yoxoallenes (see Scheme 1) and to use the methyl furanoside products obtained from such reactions in the syntheses of deoxy- and dideoxyribonucleoside analogues. Nucleoside analogues are currently of particular interest due to their ability to act as anti-tumor and anti-AIDS (Acquired Immunodeficiency Syndrome) medicines. A section of this introduction has been dedicated to information about AIDS and antiretrovlral nucleoside analogues.

A convenient route to enantiomerically pure C-nucleoslde derivatives will be mentioned as a side project. (C-Nucleosides have also been found to possess potent biological activity). In addition, the cyclizatlon of 4,5-hexadienoic acid to give butyrolactone products will be described (see Scheme 1; R'" = OH).

Palladium catalysts, Allene -- Synthesis, Nucleic acids -- Synthesis