Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions

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dc.contributor.author Gordon, Mark
dc.contributor.author Kraus, George
dc.contributor.author Li, Jun
dc.contributor.author Gordon, Mark
dc.contributor.author Kraus, George
dc.contributor.author Jensen, Jan
dc.contributor.department Chemistry
dc.date 2018-02-17T07:42:31.000
dc.date.accessioned 2020-06-30T01:19:00Z
dc.date.available 2020-06-30T01:19:00Z
dc.date.copyright Sun Jan 01 00:00:00 UTC 1995
dc.date.issued 1995-03-01
dc.description.abstract <p>Frenolicin B, an anticoccidial agent, has been synthesized in six steps from ketone 3. Racemic kalafungin, an antifungal agent, has been synthesized in five steps. The key step in both syntheses, a regioselective Diels-Alder reaction, proceeds with complete regiocontrol and in excellent yield. One rationale for the remarkable stereocontrol is that the lactone ring induces ring-puckering in the quinone subunit which, in consort with electrostatic repulsion, contributes to the regioselectivity.</p>
dc.description.comments <p>Reprinted (adapted) with permission from <em>Journal of Organic Chemistry</em> 60 (1995): 1154, doi:<a href="http://dx.doi.org/10.1021/jo00110a017" target="_blank">10.1021/jo00110a017</a>. Copyright 1995 American Chemical Society.</p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/chem_pubs/285/
dc.identifier.articleid 1272
dc.identifier.contextkey 7919690
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath chem_pubs/285
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/14729
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/285/0-L_1995_Gordon_DirectFrenolicin.pdf|||Fri Jan 14 23:11:23 UTC 2022
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/285/1995_Gordon_DirectFrenolicin.pdf|||Fri Jan 14 23:11:25 UTC 2022
dc.source.uri 10.1021/jo00110a017
dc.subject.disciplines Chemistry
dc.title Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions
dc.type article
dc.type.genre article
dspace.entity.type Publication
relation.isAuthorOfPublication 1a5927c0-5a5f-440e-86e0-9da8dc6afda0
relation.isAuthorOfPublication 773dd84a-1494-40ee-aebf-549f26a04a22
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
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