Abstract

Lyconadin A is a pentacyclic Lycopodium alkaloid isolated from the club moss Lycopodium companatum with anticancer activity. Our approach sought to incorporate a 7-exo–6-exo acyl radical cyclization cascade to access the bicyclo[5.4.0]undecane framework of lyconadin A. Our studies created methodology for the synthesis of 5-alkyl and 3,5-dialkyl-6-carbomethoxy-2-pyridones and sterically demanding epoxide substrates. These epoxide substrates underwent an unanticipated Payne rearrangement.Cranomycin is a potent antibiotic with antiprotozoal activity. Structurally it is a cyclopentane ring system with substitution at each carbon in the ring. Another interesting structural aspect is the existence of three contiguous quaternary stereocenters including two tertiary alcohols and a tert-alkylamine. Our strategy led to the development of a highly diastereoselective synthesis of vicinal tertiary diol systems. We have successfully synthesized the cyclopentenone system shown above, from which we hope to assemble cranomycin.

Degree

PhD

College and Department

Physical and Mathematical Sciences; Chemistry and Biochemistry

Rights

http://lib.byu.edu/about/copyright/

Date Submitted

2013-07-18

Document Type

Dissertation

Handle

http://hdl.lib.byu.edu/1877/etd6498

Keywords

epoxidation, pyridone synthesis, lyconadin A, tandem radical cyclization, tethered radical vinylation, Grignard addition, cranomycin

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