Towards the total synthesis of 14-acetoxygelsenicine and synthesis of largazole analogs

Herein are documented our efforts in two projects, beginning with studies towards the total synthesis of 14-acetoxygelsenicine. We have developed different strategies towards this complex natural product, wherein we have developed routes towards an appropriate substrate for a novel, intramolecular hetero Diels-Alder cyclization. The developed route would also lead to related members of this family of alkaloids, and helps set the stage for future efforts. In the second project discussed, we have successfully pursued the synthesis of numerous, biologically active analogs of the natural product (+)-largazole. Synthetic efforts have led to the design of inhibitors with unprecedented biological activity, as well as providing information regarding the structure-activity relationship of these molecules.

Name thesis:degree_name

Doctor of Philosophy (Ph.D.)

Level thesis:degree_level

Doctoral

Discipline thesis:degree_discipline

Chemistry

Grantor dc:publisher

Colorado State University. Libraries

Year dc:date.issued

2009

Authors dc:creator

• Newkirk, Tenaya L., author
• Williams, Robert M., advisor
• Stermitz, Frank R., committee member
• Ferreira, Eric M., committee member
• Rickey, Dawn, committee member
• Thamm, Douglas H., committee member

• Alkaloids -- Synthesis
• Diels-Alder reaction

Statement dc:rights

• Copyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright.

Language dc:language.iso

eng, English

Identifier URI

https://doi.org/10.25675/3.018711

OAI identifier oai:identifier

oai:mountainscholar.org:10217/235858