UBC Theses and Dissertations

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UBC Theses and Dissertations

Divinylcyclopropane rearrangements : preparation of tricyclic ring systems and a formal total synthesis of (±)-quadrone Moss, Neil


The first section of this thesis describes three model studies involving the synthesis of the divinylcyclopropanes (135), (136), and (137) and the subsequent thermal rearrangement of these compounds to provide the interesting tricyclic compounds (139), (140), and (141). [Formula Omitted] The second section of this thesis describes a formal total synthesis of the antitumor sesquiterpenoid (±)-quadrone (34). The synthesis is based on the chemistry developed in the model studies and involves the thermal rearrangement of the divinylcyclopropane (304) as the key step. The resulting product, compound (305), is- subsequently elaborated into the keto aldehyde (230), and since compound (230) has previously been converted into (t)-quadrone (34) by Burke and coworkers,¹⁰¹ the isolation of (230) comprises a formal total synthesis of the sesquiterpenoid. [Formula Omitted] The third section of this thesis describes a study involving the facile vinylmethylenecyclopropane rearrangement of enolates derived from various 7-exo-vinylbicyclo[4.1.0]heptan-2-ones.

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