An 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)
| Identifer | oai:union.ndltd.org:RICE/oai:scholarship.rice.edu:1911/16421 |
| Date | January 1991 |
| Creators | Browne, Margaret Elizabeth |
| Contributors | Ciufolini, M. A. |
| Source Sets | Rice University |
| Language | English |
| Detected Language | English |
| Type | Thesis, Text |
| Format | 260 p., application/pdf |
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