A synthesis of benzocyclobutenedione and substituted analogs was developed based on a Diels-Alder route. The benzocyclobutenediones were reacted with low valent transition metals which gave high yields of phthaloylmetal complexes (metalla-2-indane-1,3-diones). Upon reaction with alkynes the phthaloylmetal complexes gave high yields of substituted 1,4-naphthoquinones. The reaction was compatible with a variety of functionality on the alkyne. Regiochemical control of the quinone forming reaction was realized by attaching an appropriately substituted alkyne to the phthaloylmetal complex and performing the reaction in an intramolecular fashion. The resulting 11 and 13-membered macrocyclic 1,4-naphthoquinones were transformed to the pyranoquinone antibiotics isoeleutherin and nanaomycin A. / Source: Dissertation Abstracts International, Volume: 44-02, Section: B, page: 0501. / Thesis (Ph.D.)--The Florida State University, 1983.
| Identifer | oai:union.ndltd.org:fsu.edu/oai:fsu.digital.flvc.org:fsu_75061 |
| Contributors | SOUTH, MICHAEL S., Florida State University |
| Source Sets | Florida State University |
| Detected Language | English |
| Type | Text |
| Format | 163 p. |
| Rights | On campus use only. |
| Relation | Dissertation Abstracts International |
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