I The tandem chain extension-acylation reaction II Synthesis of papyracillic acid A: Application of the tandem homologation-acylation reaction III Synthesis of tetrahydrofuran-based peptidomimetics

<p>A zinc-mediated tandem chain extension-acylation reaction was successfully developed. This reaction was optimized with the use of beta-keto esters, amides, and imides as well as a variety of acylating agents. The tandem homologation-acylation reaction was successfully applied towards the total synthesis of papyracillic acid A.</p><p>Use of a tandem chain extension-aldol reaction, followed by a reductive cyclization, allowed for the synthesis of tetrahydrofuran-based peptidomimetics. A variety of amino acid derived beta-keto imides and aldehydes were used during the initial tandem homologation-aldol reaction. High diastereocontrol was achieved during reductive cyclization when a cis relationship was present between the substituents on the tetrahydrofuran ring. Use of beta-keto imides during the chain extension reaction was important as they led to the formation of the required anti-aldol products.</p>

Name thesis:degree_name

Doctor of Philosophy

Level thesis:degree_level

Dissertation

Year

2013

Author dc:creator

• Spencer, Carley Meredith

Contributors dc:contributor

• Charles K Zercher

• Chemistry
• Organic

Repository record dc:identifier

https://scholars.unh.edu/dissertation/749

OAI identifier oai:identifier

oai:scholars.unh.edu:dissertation-1748