Academic Commons

Theses Doctoral

Synthetic Innovations in Efforts Toward the Development of Spongistatin 1 as an Anti-Cancer Therapeutic

Suen, Linda Mei

A major focus of the Leighton group is on the development of chemistry to aid in the efficient and scalable synthesis of polyketides. Over the past several years, our group has been interested in utilizing strained silanes to rapidly access the structural motifs commonly found in polyketides. Notably, our EZ-CrotylMix methodology allows for the crotylation of deactivated and sterically hindered aldehydes that popular methods, such as the Brown crotylation, fail to achieve. In order to improve the practicality of our crotylation methodology, we have developed a new, more powerfully activating diamine ligand scaffold that provides access to highly active allyl- and crotyl-silanes. These silanes can be generated in situ, precluding the need for a laborious isolation of the moisture sensitive crotylsilane reagents that is necessary for our previously reported methodology. The group’s crotylation methodology has proved useful in our current efforts toward the total synthesis of spongistatin 1 and its analogs. Work on the synthesis of an analog of spongistatin 1, specifically on the completion of the northern ABCD hemisphere, will also be discussed.

Files

  • thumnail for Suen_columbia_0054D_12872.pdf Suen_columbia_0054D_12872.pdf binary/octet-stream 14.6 MB Download File

More About This Work

Academic Units
Chemistry
Thesis Advisors
Leighton, James L.
Degree
Ph.D., Columbia University
Published Here
August 11, 2015
Academic Commons provides global access to research and scholarship produced at Columbia University, Barnard College, Teachers College, Union Theological Seminary and Jewish Theological Seminary. Academic Commons is managed by the Columbia University Libraries.