Date of Award

Fall 2013

Degree Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

First Advisor

Philip L. Fuchs

Committee Chair

Philip L. Fuchs

Committee Member 1

Jean A. Chmielewski

Committee Member 2

Arun K. Ghosh

Committee Member 3

David H. Thompson

Abstract

Jamieson, Daniel P. Ph.D., Purdue University, December 2013. Continued Progress Towards Efficient Syntheses of Cephalostatin North 1 Analogs. Major Professor: PhilipL. Fuchs.

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.

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