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Synthesis Of N-Heterocycles From Donor Acceptor Cyclopropanes And Progress Towards Flinderole A, B, And C, Joanne E. Curiel Tejeda
Synthesis Of N-Heterocycles From Donor Acceptor Cyclopropanes And Progress Towards Flinderole A, B, And C, Joanne E. Curiel Tejeda
Electronic Thesis and Dissertation Repository
The first chapter of this thesis describes two projects, one explores the novel reactivity of quaternary donor acceptor cyclopropanes and the second one involves progress toward the total synthesis of the flinderoles A, B, and C. The first project involves the Lewis acid catalyzed nucleophilic ring opening of quaternary donor acceptor cyclopropanes with indoline. It was found that the ring opening reaction worked well with either Sc(OTf)3 or Yb(OTf)3 as the Lewis acids. The ring opened products were also able to be converted into pyrroloindoles via a manganese (III) oxidative radical cyclization reaction. Cyclopropanes bearing alkynyl, vinyl, and …