Studies Toward the Total Synthesis of the Lycopodium Alkaloid Spirolucidine Using the N-Acyl-2,3-dihydro-4-pyridone as a Building Block

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Title: Studies Toward the Total Synthesis of the Lycopodium Alkaloid Spirolucidine Using the N-Acyl-2,3-dihydro-4-pyridone as a Building Block
Author: Young, Damian Winston
Advisors: Daniel L. Comins, Committee Chair
Suzanne T Purrington, Committee Member
Jonathan S. Lindsey, Committee Member
Bruce M. Novak, Committee Member
Abstract: Spirolucidine is a complex alkaloid isolated from the club moss Lycopodium lucidulum. A three fragment convergent plan for the title compound was envisioned, with each fragment being derived from a chiral N-acyl-2,3-dihydro-4-pyridone. The synthesis of the bicyclic enecarbamate referred to as zone C was investigated. The first effort centered on a tandem intramolecular Diels-Alder reaction/retro Mannich ring opening reaction to set the key stereogenic centers within zone C. A second strategy aimed to ring open the tricyclic adduct which arises from the Diels-Alder reaction through an E1cB mechanism. Finally, a third attempt was made to utilize chirality transfer as a means to implement the necessary stereochemical elements of the bicyclic scaffold. The convergent union of the key fragments of spirolucidine was modeled on a simple substrate. The directed lithiation of N-Boc-dihydropyridines was utilized to prepare model 2,5,6-trisubstituted dihydropyridones of a general type needed for the completion of the spirolucidine synthesis.
Date: 2005-04-04
Degree: PhD
Discipline: Chemistry
URI: http://www.lib.ncsu.edu/resolver/1840.16/5243


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