Graduation Year

2015

Document Type

Campus Only Senior Thesis

Degree Name

Bachelor of Science

Department

Chemistry

Reader 1

David A.Vosburg

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© 2015 Eun Bin Go

Abstract

A number of natural products isolated from plants in the Endiandra and Beilschmiedia genera contain complex tetracyclic scaffolds, which are believed to be made from linear polyene precursors that undergo electrocyclization cascades. This thesis describes a concise, biomimetic and modular synthetic route to the two types of tetracyclic scaffolds that are found in these natural products. Our strategy employs iterative cross-couplings to prepare a bicyclic intermediate, which can easily be converted into each tetracycle in two more steps. This work features a novel application of Marty Burke’s iterative Suzuki-coupling method for polyene synthesis, and it represents a significant improvement over previous syntheses of endiandric acids.

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