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Uniform TitleNew methods and strategies towards total synthesis of (9S)-dihydroerythronolide A
NameGhosh, Partha (author), Williams, Lawrence (chair), Knapp, Spencer (internal member), Warmuth, Ralf (internal member), Albaneze-walker, Jennifer (outside member), Rutgers University, Graduate School - New Brunswick,
Degree Date2008-05
Date Created2008
SubjectChemistry and Chemical Biology,
Erythromycin,
Antibiotics
DescriptionDisclosed 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.
NotePh.D.
NoteIncludes bibliographical references.
Genretheses
Persistent URLhttp://hdl.rutgers.edu/1782.2/rucore10001600001.ETD.17316
LanguageEnglish
CollectionGraduate School - New Brunswick Electronic Theses and Dissertations
Organization NameRutgers, The State University of New Jersey
RightsThe author owns the copyright to this work.
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