Dihydropyridines in synthesis and biosynthesis. IV. Dehydrosecodine, in vitro precursor of indole alkaloids

JP Kutney, Y Karton, N Kawamura…

Index: Kutney, James P.; Karton, Yishai; Kawamura, Noriaki; Worth, Brian R. Canadian Journal of Chemistry, 1982 , vol. 60, p. 1269 - 1278

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Citation Number: 14

Abstract

The synthesis of the two isomeric dehydrosecodines is described. Stabilization of these systems is achieved by chromium carbonyl complexation of the dihydropyridine unit in these molecules. Reaction of the complexes with pyridine, or preferably ethylenediamine, allows in situ generation of the dehydrosecodines. A study of their chemistry and conversion to alkaloid systems is presented.