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Paper | Regular issue | Vol 26, No. 3, 1987, pp.721-730
Published online, 1st January, 1970
DOI: 10.3987/R-1987-03-0721
The Synthesis of the Isoquinoline Alkaloid Calycotomine via Functionalization of Enamide Double Bonds

George R. Lenz

*Department of Chemistry, G. D. Searle & Company, 4901 Searle ParkwaySkokie, Illinois 60077, U.S.A.

Abstract

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