Abstract
N a-BOC protected tryptophans 1 and 2 successfully undergo the Pictet-Spengler cyclization with a series of aldehydes in the presence of an acid catalyst ( p-TSA) to furnish a mixture of trans and cis 1,2,3,4-tetrahydro-β-carbolines (3 and 4). During removal of the BOC function with TFA, the mixture of trans (3) and cis (4) isomers was enantiospecifically converted into the trans N a-H 1,2,3,4-teaahydro-β-carboline 5, a key intermediate for the construction of N a,-H substituted sarpagine alkaloids.
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