Progress Toward the Total Synthesis of Paecilospirone

Author/​Artist
Landry, Matthew Leo [Browse]
Format
Senior thesis
Language
English
Description
186 pages

Details

Advisor(s)
Doyle, Abigail G. [Browse]
Department
Princeton University. Department of Chemistry [Browse]
Class year
2013
Restrictions note
Walk-in Access. This thesis can only be viewed on computer terminals at the Mudd Manuscript Library.
Summary note
Progress towards the total synthesis of paecilospirone, a microtubule inhibiting natural product, is reported. The stereochemical outcome of the proposed steps has been verified by both a computational study and the synthesis of a model system. The synthesis incorporates the use of modern methods, including organocatalytic cyclization, palladium- and nickel-catalyzed crosscouplings, and oxidative spiroketalization. The use of these methods allows for the more modular, efficient, and sustainable synthesis of a potentially valuable antitumor compound. Additionally, the incorporation of novel methods in the synthesis of a complex target demonstrates the limitations and benefits of these modern transformations, and will serve to inform their use in future syntheses.

Supplementary Information