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New methods and strategies towards total synthesis of (9S)-dihydroerythronolide A
Descriptive
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Title
New methods and strategies towards total synthesis of (9S)-dihydroerythronolide A
Name
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Ghosh
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Partha
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Partha Ghosh
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author
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Williams
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Lawrence
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Advisory Committee
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Lawrence J Williams
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chair
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Knapp
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Spencer
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Advisory Committee
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Spencer Knapp
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internal member
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Warmuth
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Ralf
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Advisory Committee
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Ralf Warmuth
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internal member
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Jennifer
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Advisory Committee
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Jennifer Albaneze-walker
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outside member
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Rutgers University
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degree grantor
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Graduate School - New Brunswick
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school
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theses
OriginInfo
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2008
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2008-05
Language
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English
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electronic
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application/pdf
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text/xml
Extent
xix, 359 pages
Abstract
Disclosed are studies directed towards the total synthesis of (9S)-dihydroerythronolide A. Towards this goal an advanced intermediate, 14 member bis[allene] macrolactone was synthesized. A general method of cuprate-mediated carbon nucleophile delivery to spirodiepoxides was developed. An unprecedented macrolactonization to form bis[allene] macrolactone and macrocyclic stereocontroled epoxidation of this system was achieved. In a separate study, the highly stereocontroled formation of spirodiepoxides and excellent regiocontroled spirodiepoxide opening was developed. This method relies upon the presence of a silyl substituent on the allene. This finding was applied to the total synthesis of epicitreodiol.
Note
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Ph.D.
Note
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Includes bibliographical references.
Subject
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Topic
Chemistry and Chemical Biology
Subject
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Topic
Erythromycin
Subject
(ID = SUBJ3);
(authority = ETD-LCSH)
Topic
Antibiotics
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Title
Graduate School - New Brunswick Electronic Theses and Dissertations
Identifier
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rucore19991600001
Identifier
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http://hdl.rutgers.edu/1782.2/rucore10001600001.ETD.17316
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ETD_761
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NjNbRU
Identifier
(type = doi)
doi:10.7282/T3057G8V
Genre
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ETD doctoral
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Rights
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The author owns the copyright to this work.
Copyright
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Copyright protected
Availability
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Open
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Name
Partha Ghosh
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Copyright holder
Affiliation
Rutgers University. Graduate School - New Brunswick
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Detail
Non-exclusive ETD license
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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.
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Technical
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15224320
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