Abstract
dc:description.abstract<p>Pyranonaphthoquinones are a class of naturally occurring antibiotics which have in common a synthetically interesting isochromanquinone skeleton. Members of this family exhibit a variety of biological activities. Examples are frenolicin B, an anticoccidial agent; kalafungin, an antifungal agent; hongconin, having cardioprotective activity against angina pectoris. Efforts toward the direct synthesis of these natural pyranonaphthoquinones forced us to develop new methodologies. During our research, a general methodology was developed to stereoselectively synthesize the common isochromanquinone skeleton. The key step in the syntheses, a regioselective Diels-Alder reaction, proceeds with complete regiocontrol and in excellent yield. This work has led to extremely direct total syntheses of hongconin, kalafungin, frenolicin B, [alpha], [beta]-epoxyfrenolicin B and their analogs.</p>
Degree
thesis:*- Name thesis:degree_name
- Doctor of Philosophy
- Level thesis:degree_level
- dissertation
- Department dc:contributor.department
- Department of Chemistry
- Year dc:date.issued
- 1994
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Li, Jun
- Advisor dc:contributor.advisor
-
- George A. Kraus
Rights
- Language dc:language.iso
- en
Identifiers
dc:identifier.*- Identifier
- archive/lib.dr.iastate.edu/rtd/10494/
- OAI identifier oai:identifier
- oai:dr.lib.iastate.edu:20.500.12876/63646