Return to search

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

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. / Science, Faculty of / Chemistry, Department of / Graduate

Identiferoai:union.ndltd.org:UBC/oai:circle.library.ubc.ca:2429/25942
Date January 1985
CreatorsMoss, Neil
PublisherUniversity of British Columbia
Source SetsUniversity of British Columbia
LanguageEnglish
Detected LanguageEnglish
TypeText, Thesis/Dissertation
RightsFor non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.

Page generated in 0.0017 seconds