Progress Toward the Synthesis of Apomorphine: Chiral Auxiliary Mediated Interception of an Intramolecularly Formed N-Acyl Iminium Ion

apomorphine;iminium ion;Horner;chiral auxiliary;Suzuki

Nuckols, Michel Christian ; Daniel L. Comins, Committee Chair,Suzanne Purrington, Committee Member,Carl Bumgardner, Committee Member,James K. Whitesell, Committee Member,Nuckols, Michel Christian ; Daniel L. Comins ; Committee Chair ; Suzanne Purrington ; Committee Member ; Carl Bumgardner ; Committee Member ; James K. Whitesell ; Committee Member

University:North Carolina State University

关键词: apomorphine;    iminium ion;    Horner;    chiral auxiliary;    Suzuki;   

Others  :  https://repository.lib.ncsu.edu/bitstream/handle/1840.16/4654/etd.pdf?sequence=1&isAllowed=y

美国|英语

来源: null

【 摘 要 】

Glaucine, which contains an aporphine skeleton, has been previously synthesized utilizing an intermolecular approach to form an iminium ion for the Pictet-Spengler reaction. A diastereomeric excess of 79% resulted as mediated by a chiral auxiliary. Progress was made in attempting to increase the diastereomeric excess by using an intramolecular approach to iminium ion formation. Apomorphine is a suitable platform on which to demonstrate the asymmetric interception of a chiral N-acyl iminium ion generated by intramolecular means.Several routes to this end were explored. These routes included the use of an intramolecular variant on the previously published work, Grubbs' metathesis and Horner-Wadsworth-Emmons among others. While no route proved successful in the end, understanding of the formation of aporphine skeletons was expanded upon.