Fragmentations of bicyclic ketoesters and synthetic efforts toward eleutherobin

Persistent Link:
http://hdl.handle.net/10150/279938
Title:
Fragmentations of bicyclic ketoesters and synthetic efforts toward eleutherobin
Author:
Xu, Qing
Issue Date:
2002
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:
An unprecedented anionic condensation, fragmentation, and elimination sequence from the coupling of bicyclo[2.2.1]heptenones with aldehydes is described. This reaction leads to the stereoselective formation of disubstituted five-membered rings which are present in a wide array of bioactive molecules. Oxabicyclo[2.2.1]heptenone 106 also undergoes two-carbon ring expansions when subjected to anionic conditions and Michael acceptors. As an outgrowth of this interesting chemistry, we have been able to access the carbon skeleton of oxygenated cembranoids by subjecting bis-activated ene-yne to the enolate from oxabicyclo[2.2.1]heptenone 106. In order to demonstrate the synthetic utility of the anionic condensation, fragmentation, and elimination reaction, we have applied it to the synthesis of nortetillapyrone.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Chemistry, Organic.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Rainier, Jon D.

Full metadata record

DC FieldValue Language
dc.language.isoen_USen_US
dc.titleFragmentations of bicyclic ketoesters and synthetic efforts toward eleutherobinen_US
dc.creatorXu, Qingen_US
dc.contributor.authorXu, Qingen_US
dc.date.issued2002en_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.abstractAn unprecedented anionic condensation, fragmentation, and elimination sequence from the coupling of bicyclo[2.2.1]heptenones with aldehydes is described. This reaction leads to the stereoselective formation of disubstituted five-membered rings which are present in a wide array of bioactive molecules. Oxabicyclo[2.2.1]heptenone 106 also undergoes two-carbon ring expansions when subjected to anionic conditions and Michael acceptors. As an outgrowth of this interesting chemistry, we have been able to access the carbon skeleton of oxygenated cembranoids by subjecting bis-activated ene-yne to the enolate from oxabicyclo[2.2.1]heptenone 106. In order to demonstrate the synthetic utility of the anionic condensation, fragmentation, and elimination reaction, we have applied it to the synthesis of nortetillapyrone.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectChemistry, Organic.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorRainier, Jon D.en_US
dc.identifier.proquest3050292en_US
dc.identifier.bibrecord.b42723644en_US
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