The Synthesis of the Isoquinoline Alkaloid Calycotomine via Functionalization of Enamide Double Bonds

HETEROCYCLES
1987.0

Abstract

The novel alkaloid calycotomine, a 1-hydroxymethylenetetrahydroisoquinoline, has been synthesized from l-methyl-3,4-dihydroisoquinoline via the 2-benzyloxycarbonyl enamide derivative. Oxidation of the enamide with osmium tetroxide results in bis-hydroxylation and ring opening to form hydroxyacetophenone carbamates. Hydrogenation results in reclosure of the isoquinoline ring and further reduction yielding 1-hydroxymethylenetetrahydro-isoquinolines. © 1987.

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