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.
","abstract_html":"<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>","abstract_has_math":false,"creators":["Li, Jun"],"institution":null,"degree_name":"Doctor of Philosophy","degree_level":"dissertation","degree_discipline":null,"degree_department":"Department of Chemistry","school":null,"contributors":[],"advisors":["George A. Kraus"],"committee_chairs":[],"committee_members":[],"year":1994,"date_issued":"1994","date_published":"1994","updated_at":"2026-07-24T02:38:12Z","subjects":[],"languages":["en"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier.doi","label":"DOI","values":["https://doi.org/10.31274/rtd-180813-12358"],"render_values":[{"text":"https://doi.org/10.31274/rtd-180813-12358","href":"https://doi.org/10.31274/rtd-180813-12358","code":true}]},{"key":"dc:identifier","label":"Identifier","values":["archive/lib.dr.iastate.edu/rtd/10494/"],"render_values":[{"text":"archive/lib.dr.iastate.edu/rtd/10494/","href":null,"code":true}]}]},"links":{"outbound_url":"https://dr.lib.iastate.edu/handle/20.500.12876/63646","outbound_label":"Repository record","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["George A. Kraus"]},{"key":"dc:contributor.department","label":"Department","values":["Department of Chemistry"]},{"key":"dc:creator","label":"Author","values":["Li, Jun"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2018-08-23T18:03:32.000"]},{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2020-06-30T07:05:17Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2020-06-30T07:05:17Z"]},{"key":"dc:date.issued","label":"Date","values":["1994"]},{"key":"dc:type","label":"Dc Type","values":["dissertation"]},{"key":"thesis:degree_level","label":"Degree Level","values":["dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Doctor of Philosophy"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["en"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["archive/lib.dr.iastate.edu/rtd/10494/"]},{"key":"dc:identifier.doi","label":"DOI","values":["https://doi.org/10.31274/rtd-180813-12358"]},{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://dr.lib.iastate.edu/handle/20.500.12876/63646"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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.
"]},{"key":"dc:format.mimetype","label":"Dc Format Mimetype","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Total synthesis of pyranonaphthoquinone natural products"]}]}],"canonical_facts":{"dc:contributor.advisor":["George A. Kraus"],"dc:contributor.department":["Department of Chemistry"],"dc:creator":["Li, Jun"],"dc:date":["2018-08-23T18:03:32.000"],"dc:date.accessioned":["2020-06-30T07:05:17Z"],"dc:date.available":["2020-06-30T07:05:17Z"],"dc:date.issued":["1994"],"dc:description.abstract":["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.
"],"dc:format.mimetype":["application/pdf"],"dc:identifier":["archive/lib.dr.iastate.edu/rtd/10494/"],"dc:identifier.doi":["https://doi.org/10.31274/rtd-180813-12358"],"dc:identifier.uri":["https://dr.lib.iastate.edu/handle/20.500.12876/63646"],"dc:language.iso":["en"],"dc:title":["Total synthesis of pyranonaphthoquinone natural products"],"dc:type":["dissertation"],"thesis:degree_level":["dissertation"],"thesis:degree_name":["Doctor of Philosophy"]},"updated_at":"2026-07-24T02:38:12Z"}