RUcore: Rutgers University Community Repository
Allene-based approach to the synthesis of De Novo erythromycinoids
Descriptive
TitleInfo
Title
Allene-based approach to the synthesis of De Novo erythromycinoids
Name
(type = personal)
NamePart
(type = family)
Kim
NamePart
(type = given)
Hiyun
DisplayForm
Hiyun Kim
Role
RoleTerm
(authority = RULIB)
author
Name
(type = personal)
NamePart
(type = family)
Williams
NamePart
(type = given)
Lawrence J
DisplayForm
Lawrence J Williams
Affiliation
Advisory Committee
Role
RoleTerm
(authority = RULIB)
chair
Name
(type = personal)
NamePart
(type = family)
Warmuth
NamePart
(type = given)
Ralf
DisplayForm
Ralf Warmuth
Affiliation
Advisory Committee
Role
RoleTerm
(authority = RULIB)
internal member
Name
(type = personal)
NamePart
(type = family)
Hultzsch
NamePart
(type = given)
Kai C
DisplayForm
Kai C Hultzsch
Affiliation
Advisory Committee
Role
RoleTerm
(authority = RULIB)
internal member
Name
(type = personal)
NamePart
(type = family)
Hu
NamePart
(type = given)
Longqin
DisplayForm
Longqin Hu
Affiliation
Advisory Committee
Role
RoleTerm
(authority = RULIB)
outside member
Name
(type = corporate)
NamePart
Rutgers University
Role
RoleTerm
(authority = RULIB)
degree grantor
Name
(type = corporate)
NamePart
Graduate School - New Brunswick
Role
RoleTerm
(authority = RULIB)
school
TypeOfResource
Text
Genre
(authority = marcgt)
theses
OriginInfo
DateCreated
(qualifier = exact)
2012
DateOther
(qualifier = exact);
(type = degree)
2012-01
CopyrightDate
(qualifier = exact)
2012
Place
PlaceTerm
(type = code)
xx
Language
LanguageTerm
(authority = ISO639-2b);
(type = code)
eng
Abstract
(type = abstract)
We prepared an advanced synthetic module (bis[allene] macrolactone at center) equipped with two allenes embedded in a macrolactone scaffold. The plan was to effect heterogeneous derivatization of the allenes, in tandem or separately. In addition to diversity, this approach is maximally concise and economic, especially in terms of steps. Moreover, immediate derivatives of the macrocyclic bis[allene] can be taken into further steps, thus providing canonical build-up of erythromycin analogs. To date, our bis[allene] macrolactone has been converted to over 30 novel macrolides. These de novo analogs serve to validate the strategy and lay the ground work for further work. Taken together, the allene-based reactions/transformations employed in this study, such as DMDO oxidation/nucleophile addition, allene osmylation/electrophile addition, bromination, allene oxide rearrangement, spirodiepoxide rearrangement, benzylic migration/elimination, mono- and bis-oxidation of bis[allene], chelation-controlled reduction and oxime formation, demonstrate that 8 of the 11 modifiable carbons in this antibiotic can be modified. It is especially noteworthy that each congener was made in less than three steps from the bis[allene] macrolactone.
Subject
(authority = RUETD)
Topic
Chemistry and Chemical Biology
RelatedItem
(type = host)
TitleInfo
Title
Rutgers University Electronic Theses and Dissertations
Identifier
(type = RULIB)
ETD
Identifier
ETD_3735
PhysicalDescription
Form
(authority = gmd)
electronic resource
InternetMediaType
application/pdf
InternetMediaType
text/xml
Extent
xxi, 691 p. : ill.
Note
(type = degree)
Ph.D.
Note
(type = bibliography)
Includes bibliographical references
Note
(type = vita)
Includes vita
Note
(type = statement of responsibility)
by Hiyun Kim
Subject
(authority = ETD-LCSH)
Topic
Allene--Research
Identifier
(type = hdl)
http://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000064137
RelatedItem
(type = host)
TitleInfo
Title
Graduate School - New Brunswick Electronic Theses and Dissertations
Identifier
(type = local)
rucore19991600001
Location
PhysicalLocation
(authority = marcorg);
(displayLabel = Rutgers, The State University of New Jersey)
NjNbRU
Identifier
(type = doi)
doi:10.7282/T39W0DHJ
Genre
(authority = ExL-Esploro)
ETD doctoral
Back to the top
Rights
RightsDeclaration
(ID = rulibRdec0006)
The author owns the copyright to this work.
RightsHolder
(type = personal)
Name
FamilyName
Kim
GivenName
Hiyun
Role
Copyright Holder
RightsEvent
Type
Permission or license
DateTime
(encoding = w3cdtf);
(qualifier = exact);
(point = start)
2011-12-16 02:55:56
AssociatedEntity
Name
Hiyun Kim
Role
Copyright holder
Affiliation
Rutgers University. Graduate School - New Brunswick
AssociatedObject
Type
License
Name
Author Agreement License
Detail
I hereby grant to the Rutgers University Libraries and to my school the non-exclusive right to archive, reproduce and distribute my thesis or dissertation, in whole or in part, and/or my abstract, in whole or in part, in and from an electronic format, subject to the release date subsequently stipulated in this submittal form and approved by my school. I represent and stipulate that the thesis or dissertation and its abstract are my original work, that they do not infringe or violate any rights of others, and that I make these grants as the sole owner of the rights to my thesis or dissertation and its abstract. I represent that I have obtained written permissions, when necessary, from the owner(s) of each third party copyrighted matter to be included in my thesis or dissertation and will supply copies of such upon request by my school. I acknowledge that RU ETD and my school will not distribute my thesis or dissertation or its abstract if, in their reasonable judgment, they believe all such rights have not been secured. I acknowledge that I retain ownership rights to the copyright of my work. I also retain the right to use all or part of this thesis or dissertation in future works, such as articles or books.
Copyright
Status
Copyright protected
Availability
Status
Open
Reason
Permission or license
Back to the top
Technical
FileSize
(UNIT = bytes)
35358720
Checksum
(METHOD = SHA1)
1b6176784f355843e012b128b18f8b5c7008f10e
OperatingSystem
(VERSION = 5.1)
windows xp
ContentModel
ETD
MimeType
(TYPE = file)
application/pdf
Back to the top
Statistical Profile