Persistent Link:
http://hdl.handle.net/10150/184428
Title:
Synthetic approach to bonandiol and hyperforin.
Author:
Heidt, Philip Conrad.
Issue Date:
1988
Publisher:
The University of Arizona.
Rights:
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Abstract:
The enantioselective approach to bonandiol, also known as magydardiendiol, has utilized two novel synthetic methodologies. The first is the diastereoselective cyclopropanation of a homochiral eneketal prepared from (2R,3R)- or (2S,3S)-2,3-butanediol and possessing C₂ symmetry. Simmons-Smith cyclopropanation gave good diastereoselectivity (69-75%) in addition to excellent amounts of monocyclopropanated material obtained (90-96%). The second method utilized is the nickel acetylacetonate catalyzed coupling of dimethylzinc to a sterically hindered cyclic β-keto enolphosphate in 76-92% yield. This approach to the A ring of hyperforin starting from commercially available citral allows for the introduction of all but one isoprenyl appendage.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Natural products -- Synthesis.; Diterpenes -- Synthesis.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Chemistry; Graduate College
Degree Grantor:
University of Arizona
Advisor:
Mash, Eugene

Full metadata record

DC FieldValue Language
dc.language.isoenen_US
dc.titleSynthetic approach to bonandiol and hyperforin.en_US
dc.creatorHeidt, Philip Conrad.en_US
dc.contributor.authorHeidt, Philip Conrad.en_US
dc.date.issued1988en_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.description.abstractThe enantioselective approach to bonandiol, also known as magydardiendiol, has utilized two novel synthetic methodologies. The first is the diastereoselective cyclopropanation of a homochiral eneketal prepared from (2R,3R)- or (2S,3S)-2,3-butanediol and possessing C₂ symmetry. Simmons-Smith cyclopropanation gave good diastereoselectivity (69-75%) in addition to excellent amounts of monocyclopropanated material obtained (90-96%). The second method utilized is the nickel acetylacetonate catalyzed coupling of dimethylzinc to a sterically hindered cyclic β-keto enolphosphate in 76-92% yield. This approach to the A ring of hyperforin starting from commercially available citral allows for the introduction of all but one isoprenyl appendage.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectNatural products -- Synthesis.en_US
dc.subjectDiterpenes -- Synthesis.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorMash, Eugeneen_US
dc.contributor.committeememberBates, Roberten_US
dc.contributor.committeememberHruby, Victoren_US
dc.contributor.committeememberRund, Johnen_US
dc.contributor.committeememberLaw, Johnen_US
dc.identifier.proquest8816313en_US
dc.identifier.oclc701248920en_US
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