Synthetic studies of indoles and related compounds. XXVII. A new synthesis of crenatine from ethyl indole-2-carboxylate

Article abstract of DOI:10.1248/cpb.39.2189

Crenatine (1a), which is a member of a new class of β-carboline alkaloids having an oxygen functionality at the 4-position, was synthesized starting from ethyl 1-benzylindole-2-carboxylate (12a) via cyclization of an elaborated C₂-substituent to the 3-position of the indole nucleus and aluminum chloride-catalyzed debenzylation of the protected indolic nitrogen. 1-Ethyl-4-hydroxy-9-methyl-β-carboline (26b), a positional isomer of crenatine with regard to the methyl group, was also synthesized through the same methodology.

Full text of DOI:10.1248/cpb.39.2189

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