Progress Toward the Total Synthesis of Garsubellin A and Structurally Related Phloroglucin Natural Products

Citation

Spessard, Sarah Jane (2003) Progress Toward the Total Synthesis of Garsubellin A and Structurally Related Phloroglucin Natural Products. Master's thesis, California Institute of Technology. doi:10.7907/1y2w-nn41. https://resolver.caltech.edu/CaltechTHESIS:03142025-165919678

Abstract

Progress toward the polyprenylated phloroglucin garsubellin A is presented. A highly diastereoselective single-step cyclization reaction provides access to the bicyclo[3.3.1]nonane core of this natural product. Further elaboration to a more functionalized analog involves a sequential Claisen rearrangement/Grubbs olefin cross metathesis strategy. Additionally, the feasibility of this strategy toward the preparation of the bis-quaternary carbon array found at the bridgehead positions of the phloroglucinol natural products is demonstrated. Enantioselective strategies and model studies will also be discussed.

Thesis Files