Catalyst Design for Asymmetric Organozinc Addition to Aldehydes and Progress Toward the Total Synthesis of the Marine Alkaloid, (-)-Lepadiformine.

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Title: Catalyst Design for Asymmetric Organozinc Addition to Aldehydes and Progress Toward the Total Synthesis of the Marine Alkaloid, (-)-Lepadiformine.
Author: Marks, Lucas Richard
Advisors: Daniel L. Comins, Committee Chair
Christian Melander, Committee Member
Suzanne T. Purrington, Committee Member
T. Brent Gunnoe, Committee Member
Abstract: A novel dihydropyridone was synthesized in search for a chiral ligand for the asymmetric addition of an alkyl group to an aldehyde. The target amine was derived from an enamine through a hydrogenation reaction. A study directed toward the total synthesis of the marine alkaloid (-)-lepadiformine was carried out. Two approaches were investigated toward the core perhydroquinoline system. The first approach utilized a Grignard addition to an N-acylpyridinium salt and a [2+2] photochemical addition as the key synthetic steps. The second approach was based upon quinoline chemistry. The model study was completed with a one-carbon alkene homologation to form a terminal butane. An asymmetric route was examined.
Date: 2006-05-10
Degree: EdD
Discipline: Chemistry
URI: http://www.lib.ncsu.edu/resolver/1840.16/5357


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