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Spirodiepoxide-based cascade strategies to the upper hemisphere of pectenotoxin-4

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TitleInfo
Title
Spirodiepoxide-based cascade strategies to the upper hemisphere of pectenotoxin-4
Name (type = personal)
NamePart (type = family)
Xu
NamePart (type = given)
Da
NamePart (type = date)
1986-
DisplayForm
Da Xu
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)
Daniel
NamePart (type = given)
Seidel
DisplayForm
Seidel Daniel
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
internal member
Name (type = personal)
NamePart (type = family)
Roger
NamePart (type = given)
Jones A
DisplayForm
Jones A Roger
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
internal member
Name (type = personal)
NamePart (type = family)
Zhao
NamePart (type = given)
Hong
DisplayForm
Hong Zhao
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)
2014
DateOther (qualifier = exact); (type = degree)
2014-10
CopyrightDate (encoding = w3cdtf)
2014
Place
PlaceTerm (type = code)
xx
Language
LanguageTerm (authority = ISO639-2b); (type = code)
eng
Abstract (type = abstract)
Disclosed are studies on allene oxidations and functionally diverse motif. The utilization of spirodiepoxide based methodologies in the synthesis of highly functionalized α-tetrahydrofuranyl-α'-hydroxy ketones led to a cascade strategy to the upper hemisphere of pectenotoxin-4. Remarkably, an advanced allene intermediate with six stereo centers and one epoxide was converted to a C1-C19 sector of pectenotoxin-4 with 9 stereo centers including 3 rings in one pot and 26% yield. It is also shown that electrophile capture with osmium enolates resulted in anti-α-halo-α’-hydroxyketone products. This method complements our spirodiepoxide chemistry in stereroselective conversion of chiral allenes. Finally, we envisioned that a cyclodecatrienone, prepared via C-C fragmentation of a cis-decalin derivative, could be built up to Vernonia allenes and other structurally related germacranes by taking advantage of our allene chemistry.
Subject (authority = RUETD)
Topic
Chemistry and Chemical Biology
Subject (authority = ETD-LCSH)
Topic
Ketones
Subject (authority = ETD-LCSH)
Topic
Allene
Subject (authority = ETD-LCSH)
Topic
Fragmentation reactions
RelatedItem (type = host)
TitleInfo
Title
Rutgers University Electronic Theses and Dissertations
Identifier (type = RULIB)
ETD
Identifier
ETD_5871
PhysicalDescription
Form (authority = gmd)
electronic resource
InternetMediaType
application/pdf
InternetMediaType
text/xml
Extent
1 online resource (x, 393 p. : ill.)
Note (type = degree)
Ph.D.
Note (type = bibliography)
Includes bibliographical references
Note (type = statement of responsibility)
by Da Xu
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/T3HH6MQ2
Genre (authority = ExL-Esploro)
ETD doctoral
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Rights

RightsDeclaration (ID = rulibRdec0006)
The author owns the copyright to this work.
RightsHolder (type = personal)
Name
FamilyName
Xu
GivenName
Da
Role
Copyright Holder
RightsEvent
Type
Permission or license
DateTime (encoding = w3cdtf); (qualifier = exact); (point = start)
2014-09-21 23:16:01
AssociatedEntity
Name
DA XU
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
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Technical

RULTechMD (ID = TECHNICAL1)
ContentModel
ETD
OperatingSystem (VERSION = 5.1)
windows xp
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