Syntheses and transformation of tetrahydrofuran-containing substrates: synthetic approaches to the upper portion of Pamamycin-607

Date

1993-12

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Publisher

Texas Tech University

Abstract

Organic chemistry is the chemistry of the compounds of carbon. Of ali the principal constituent parts of organic chemistry, synthesis is the one with the longest history and has constituted the most important part from the very beginning of the subject.

Production of a new synthetic methodology to achieve a specific transformation, such as the introduction of functional groups into a molecule, the interconversion of functional groups, and the development of new reagents bave been the continuous desire and motivation of synthetic organic chemists. This dissertation, intrigued by the above motives, describes the investigation of new synthetic methodologies and synthetic studies on a naturai product, in two separate parts.

The first part of this dissertation describes an attempt to develop new synthetic methodologies for the construction of the substituted tetrahydrofuran units and the transformations of some of the products obtained using that methodology. This research is valuable and stimulated by the recent isolation and characterization of numerous tetrahydrofuran-containing antibiotics and polyethers.

The second part of this dissertation describes synthetic work toward the novel autoregulatory agent and antibiotic pamamycin-607. Its biologica! activity, anion transport activity and potentially useful antibiotic activity qualify pamamycin-607 as an excellent target for total synthesis.

This dissertation, the combination of two different parts, investigates new synthetic methodologies which are useful and widely applicable to the synthesis of polyether and macrolide antibiotics.

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