Ciufolini, Marco A.2009-06-042009-06-041991Browne, Margaret Elizabeth. "Synthetic studies toward an advanced intermediate of Fredericamycin A and the development and application of a novel palladium(0)-mediated spiroarylation." (1991) Diss., Rice University. <a href="https://hdl.handle.net/1911/16421">https://hdl.handle.net/1911/16421</a>.https://hdl.handle.net/1911/16421An advanced intermediate 2 for the synthesis of antitumor antibiotic ($\pm$)-Fredericamycin $A$, 1, has been prepared. The synthetic route features a novel palladium(0)-mediated intramolecular spiroarylation of 3. This methodology allows access to the unusual spirocyclic ring skeleton characteristic of Fredericamycin $A$ from more readily accessible precursors, isoquinoline 4 and naphthalide 5. The syntheses of 4 and 5 are discussed. Preliminary model studies established an efficient pathway to structures related to 3. These initial studies also disclosed a means by which to generate spirocyclic ring systems of the type found in Fredericamycin $A$. (DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI)260 p.application/pdfengCopyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.Organic chemistryPharmaceutical chemistryThesisThesis Chem. 1991 Browne