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.
","abstract_html":"<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>","abstract_has_math":false,"creators":["Jamieson, Daniel Preston"],"institution":null,"degree_name":"Doctor of Philosophy (PhD)","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Philip L. Fuchs","Jean A. Chmielewski","Arun K. Ghosh","David H. Thompson"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2013,"date_issued":"2013-10-01T07:00:00Z","date_published":"2013-10-01T07:00:00Z","updated_at":"2026-07-24T03:53:02Z","subjects":["pure sciences","27-dihydroxy cepaholstatin north 1","cephalostatin north 1","Red-ox","spiroketals","synthesis","takeda coupling","Organic Chemistry"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://docs.lib.purdue.edu/open_access_dissertations/160","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Philip L. Fuchs","Jean A. Chmielewski","Arun K. Ghosh","David H. Thompson"]},{"key":"dc:creator","label":"Author","values":["Jamieson, Daniel Preston"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Doctor of Philosophy (PhD)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["pure sciences","27-dihydroxy cepaholstatin north 1","cephalostatin north 1","Red-ox","spiroketals","synthesis","takeda coupling","Organic Chemistry"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://docs.lib.purdue.edu/open_access_dissertations/160"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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.
"]},{"key":"dc:title","label":"Title","values":["Continued Progress Towards Efficient Syntheses Of Cephalostatin North 1 Analogs"]}]}],"canonical_facts":{"dc:contributor":["Philip L. Fuchs","Jean A. Chmielewski","Arun K. Ghosh","David H. Thompson"],"dc:creator":["Jamieson, Daniel Preston"],"dc:description.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.
"],"dc:identifier":["https://docs.lib.purdue.edu/open_access_dissertations/160"],"dc:subject":["pure sciences","27-dihydroxy cepaholstatin north 1","cephalostatin north 1","Red-ox","spiroketals","synthesis","takeda coupling","Organic Chemistry"],"dc:title":["Continued Progress Towards Efficient Syntheses Of Cephalostatin North 1 Analogs"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Doctor of Philosophy (PhD)"]},"updated_at":"2026-07-24T03:53:02Z"}