RUcore Resource Object
RUcore Resource Object
TitleFormation and reactivity of allenes and spirodiepoxides
NameZhang, Yue (author), Williams, Lawrence J (chair), Knapp, Spencer (internal member), Warmuth, Ralf (internal member), Hu, Longqin (outside member), Rutgers University, Graduate School - New Brunswick,
Degree Date2010-10
Date Created2010
SubjectChemistry and Chemical Biology,
Allene--Oxidation,
Allene--Reactivity
DescriptionDisclosed are the studies on allene and functionalized medium sized ring synthesis as well as applications of spirodiepoxide based methods. A new method of making allenes via C-C bond fragmentation was developed by which, most notably, an enantioenriched functionalized cyclic allene was synthesized. Mechanistic studies provide a framework for understanding this reaction in relation to other known modes of fragmentation. The synthesis of a chiral cyclononadienone was completed. This product has been shown to be a key intermediate towards many members of the xenicane family. Three epoxomicin analogues were synthesized. The issue of selectivity in allene oxidation was addressed in the course of this study. A model study towards erythronolide A was completed in which the feasibility of selective double cuprate addition to a bis[spirodiepoxide] macrolactone controlled by the macrocyclic environment was demonstrated. Lastly, the development of new reactions using spirodiepoxides to directly access densely functionalized structures in single- or two-flask procedures is reported.
NotePh.D.
NoteIncludes bibliographical references
NoteIncludes vita
Noteby Yue Zhang
Genretheses
Persistent URLhttp://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000056874
Languageeng
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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