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,
SubjectChemistry and Chemical Biology,
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.
NoteIncludes bibliographical references
Noteby Yue Zhang
CollectionGraduate School - New Brunswick Electronic Theses and Dissertations
Organization NameRutgers, The State University of New Jersey
RightsThe author owns the copyright to this work.