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.
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.
","abstract_html":"<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>","abstract_has_math":false,"creators":["Spencer, Carley Meredith"],"institution":null,"degree_name":"Doctor of Philosophy","degree_level":"Dissertation","degree_discipline":null,"degree_department":null,"school":null,"contributors":["Charles K Zercher"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2013,"date_issued":"2013-01-01T08:00:00Z","date_published":"2013-01-01T08:00:00Z","updated_at":"2026-07-24T05:22:42Z","subjects":["Chemistry","Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://scholars.unh.edu/dissertation/749","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Charles K Zercher"]},{"key":"dc:creator","label":"Author","values":["Spencer, Carley Meredith"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Doctor of Philosophy"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry","Organic"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://scholars.unh.edu/dissertation/749"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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.
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.
"]},{"key":"dc:title","label":"Title","values":["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"]}]}],"canonical_facts":{"dc:contributor":["Charles K Zercher"],"dc:creator":["Spencer, Carley Meredith"],"dc:description.abstract":["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.
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.
"],"dc:identifier":["https://scholars.unh.edu/dissertation/749"],"dc:subject":["Chemistry","Organic"],"dc:title":["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"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Doctor of Philosophy"]},"updated_at":"2026-07-24T05:22:42Z"}