Studies on indian medicinal plants : part 91 1 -structure and synthesis of alamaridine, a novel 5-methylbenzopyrioquinolizine alkaloid from

Tetrahedron
1988.0

Abstract

The structure of alamaridine (1) a novel benzopyridoquinolizine alkaloid, was established by spectral data. However, its stereochemistry could only be determined now by a total synthesis involving the key cyclisation of an 1-methyl-2-pyridylmethyl-3,4-dihydroisoquinolinium salt 19a in presence of pivaloyl chloride and triethylamine. O-Benzyldehydroalamaridine thus formed was reduced by sodium cyanoborohydride and then deprotected to obtain alamaridine (1) and 5-epi-alamaridine (26). Isoalamaridine (27) and its 5-epimer (28) were also synthesised following the same route. © 1988.

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