Studies in asymmetric synthesis: Development of new synthetic methods for syntheses of natural products.

Persistent Link:
http://hdl.handle.net/10150/186538
Title:
Studies in asymmetric synthesis: Development of new synthetic methods for syntheses of natural products.
Author:
Nimkar, Sandeep Krishnaji.
Issue Date:
1993
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 research, to be discussed in three chapters, involves the development of new synthetic methods which are applicable to the total synthesis of many natural products. Chapter 1: As a part of a program to synthesize new auxiliary agents for asymmetric synthesis, we have prepared a structurally rigid acetal from norbornene in three chemical steps. This enantiomerically pure acetal has been used for resolution of racemic α-hydroxy esters and might be applied as a chiral auxiliary for diastereoselective reactions. Chapter 2: The Calicheamicin and Esperamicin antibiotics have shown remarkable biological activity as site-specific cleaving agents of double stranded DNA. The oligosaccharide portion of these molecules plays an important role in the site specificity. We have developed synthetic methodologies that allow synthesis of the deoxyaminosugar components of these antibiotics and can be extended to synthesize unnatural amino sugars for structure-activity studies. Chapter 3: Enantiomerically pure cyclopropyl ketones, which are available via chiral ketals, are very useful for syntheses and diastereoselective manipulations of common and large rings. This method has been extended to introduce up to four contiguous chiral centers in a common ring. This extension could be useful for the syntheses of complex natural products.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Dissertations, Academic.; Chemistry, Organic.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Chemistry; Graduate College
Degree Grantor:
University of Arizona
Committee Chair:
Mash, Eugene A. Jr.

Full metadata record

DC FieldValue Language
dc.language.isoenen_US
dc.titleStudies in asymmetric synthesis: Development of new synthetic methods for syntheses of natural products.en_US
dc.creatorNimkar, Sandeep Krishnaji.en_US
dc.contributor.authorNimkar, Sandeep Krishnaji.en_US
dc.date.issued1993en_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 research, to be discussed in three chapters, involves the development of new synthetic methods which are applicable to the total synthesis of many natural products. Chapter 1: As a part of a program to synthesize new auxiliary agents for asymmetric synthesis, we have prepared a structurally rigid acetal from norbornene in three chemical steps. This enantiomerically pure acetal has been used for resolution of racemic α-hydroxy esters and might be applied as a chiral auxiliary for diastereoselective reactions. Chapter 2: The Calicheamicin and Esperamicin antibiotics have shown remarkable biological activity as site-specific cleaving agents of double stranded DNA. The oligosaccharide portion of these molecules plays an important role in the site specificity. We have developed synthetic methodologies that allow synthesis of the deoxyaminosugar components of these antibiotics and can be extended to synthesize unnatural amino sugars for structure-activity studies. Chapter 3: Enantiomerically pure cyclopropyl ketones, which are available via chiral ketals, are very useful for syntheses and diastereoselective manipulations of common and large rings. This method has been extended to introduce up to four contiguous chiral centers in a common ring. This extension could be useful for the syntheses of complex natural products.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectDissertations, Academic.en_US
dc.subjectChemistry, Organic.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.chairMash, Eugene A. Jr.en_US
dc.contributor.committeememberHall, Henry K. Jr.en_US
dc.contributor.committeememberMulvaney, James E.en_US
dc.contributor.committeememberWigley, David E.en_US
dc.contributor.committeememberRemers, William A.en_US
dc.identifier.proquest9421745en_US
dc.identifier.oclc721928900en_US
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