Chemical Communications 2012-12-28

Total syntheses of mitragynine, paynantheine and speciogynine via an enantioselective thiourea-catalysed Pictet-Spengler reaction.

Isabel P Kerschgens, Elise Claveau, Martin J Wanner, Steen Ingemann, Jan H van Maarseveen, Henk Hiemstra

Index: Chem. Commun. (Camb.) 48(100) , 12243-5, (2012)

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Abstract

The pharmacologically interesting indole alkaloids (-)-mitragynine, (+)-paynantheine and (+)-speciogynine were synthesised in nine steps from 4-methoxytryptamine by a route featuring (i) an enantioselective thiourea-catalysed Pictet-Spengler reaction, providing the tetrahydro-β-carboline ring and (ii) a Pd-catalysed Tsuji-Trost allylic alkylation, closing the D-ring.