Date of Award:
Master of Science (MS)
Chemistry and Biochemistry
Daniel L. Comins
The most efficient and stereoselective total synthesis of (+/-) lausbine II to date has been achieved. The key steps in this are the copper-mediated conjugate addition reaction of the Grignard reagent of 1-bromo-4-chlorobutane to a dihydropyridone and a stereoselective reduction of a quinolizidinone.
Methodology has been developed for the convenient synthesis of 1-acyl-2-substituted-1,2,5,6-tetrahydropyridines. This was accomplished by adding novel alkylzinc iodides to the 1-acyliminium ion derived from Nphenoxycarbonyl-4-methoxy-1, 2, 3, 4-tetrahydropyridine.
Foley, Michael Andrew, "1-Acyldihydropyridones as Synthetic Intermediates" (1988). All Graduate Theses and Dissertations. 7180.
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