Synthesis of the Tetracyclic Scaffolds of the Endiandric Acids
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...
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Scholarship @ Claremont
2015
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| Online Access: | http://scholarship.claremont.edu/hmc_theses/68 http://scholarship.claremont.edu/cgi/viewcontent.cgi?article=1071&context=hmc_theses |
| Summary: | 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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