Continued Progress Towards Efficient Syntheses Of Cephalostatin North 1 Analogs

<p>Jamieson, Daniel P. Ph.D., Purdue University, December 2013. Continued Progress Towards Efficient Syntheses of Cephalostatin North 1 Analogs. Major Professor: PhilipL. Fuchs.</p> <p>The cephalostatins and ritterazines represent an intriguing class of marine natural products in both structure and biological activity, and the progress towards the synthesis of high valued analogs with a focus on process orientated methodology is described herein. Included in the pages to follow, is the further advancement of the `Red-Ox' strategy toward the highly efficient synthesis of 25-epi-4,15-dihydro-North 1, Chapter 2. A short review focusing on the earlier efforts toward the main synthetic challenges of North 1 analogs and the lessons learned to propel the efficient stereoselective synthesis of anti-cancer spiroketals is presented. The development of a new Plug and Play' titanium(II) alkylidenation approach for the synthesis of α-functionalized spiroketals is presented in Chapter 3. Highlighting the new strategy, is the process efficient synthesis of the a key enol ether intermediate as the gateway to the synthesis of 26,27-dihydroxy North 1 and other spiroketal analogs. The use of silyl triflates for tandem one pot kinetic resolution of diastereomers is also presented.</p>

Name thesis:degree_name

Doctor of Philosophy (PhD)

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Year

2013

Author dc:creator

• Jamieson, Daniel Preston

Contributors dc:contributor

• Philip L. Fuchs
• Jean A. Chmielewski
• Arun K. Ghosh
• David H. Thompson

• pure sciences
• 27-dihydroxy cepaholstatin north 1
• cephalostatin north 1
• Red-ox
• spiroketals
• synthesis
• takeda coupling
• Organic Chemistry

Repository record dc:identifier

https://docs.lib.purdue.edu/open_access_dissertations/160

OAI identifier oai:identifier

oai:docs.lib.purdue.edu:open_access_dissertations-1055