Abstract
The synthesis [from D(+)-tryptophan] of the tetracyclic ketone [(−)-1b] was carried out in enantiospecifc fashion (>98% ee) via the 1,3-transfer of chirality from N a -methyl, N b -benzyl tryptophan methyl ester [(+)-14] to the trans diastereomer [(−)-4b] in the Pictet-Spengler reaction. Although the condensation of 14 with aldehyde (15) in refluxing benzene generated the tetrahydro β-carbolines (4b/5b) in a kinetic ratio (72:28), epimerization (C-1) of the cis diastereomer [(+)-5b] into the trans isomer [(−)-4b] occurred stereospecifically under acidic conditions
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