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

heterocycles;spirolucidine;alkaloids;dihydropyridones

Young, Damian Winston ; Daniel L. Comins, Committee Chair,Suzanne T Purrington, Committee Member,Jonathan S. Lindsey, Committee Member,Bruce M. Novak, Committee Member,Young, Damian Winston ; Daniel L. Comins ; Committee Chair ; Suzanne T Purrington ; Committee Member ; Jonathan S. Lindsey ; Committee Member ; Bruce M. Novak ; Committee Member

University:North Carolina State University

关键词: heterocycles;    spirolucidine;    alkaloids;    dihydropyridones;   

Others  :  https://repository.lib.ncsu.edu/bitstream/handle/1840.16/5243/etd.pdf?sequence=1&isAllowed=y

美国|英语

来源: null

【 摘 要 】

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.