Vinylogous Esters and Amides: Useful Synthons for Diversity-Oriented and Natural Product Synthesis
Issue Date
2009-05-04Author
Leighty, Matthew
Publisher
University of Kansas
Format
157 pages
Type
Dissertation
Degree Level
Ph.D.
Discipline
Medicinal Chemistry
Rights
This item is protected by copyright and unless otherwise specified the copyright of this thesis/dissertation is held by the author.
Metadata
Show full item recordAbstract
The first total synthesis of boehmeriasin A was achieved in seven steps from readily available materials with an overall yield of 29%. The absolute stereochemistry of the natural product was determined to be of the (R)-configuration. (-)-(R)-Boehmeriasin A demonstrated potent cytotoxicity in several cancer cell lines including drug resistant cancer cells where paclitaxel is inactive. An efficient and mild method for the construction if chromones was developed that requires only a single purification step at the end of the sequence and results in moderate to good yields of the isolated chromones. This method was applied toward the synthesis of 5-hydroxy-2-(2-phenylethyl)chromone, a neuroprotective chromone. The reduction of tertiary amides using Cp2Zr(H)Cl to the corresponding aldehydes on a preparatory scale results in good isolated yields of the products. Through a modified workup procedure, issues not previously observed were overcome to afford good isolated yields of the corresponding aldehydes.
Collections
Items in KU ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.
We want to hear from you! Please share your stories about how Open Access to this item benefits YOU.