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Issue 100, 2012
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Total syntheses of mitragynine, paynantheine and speciogynine via an enantioselective thiourea-catalysed Pictet–Spengler reaction

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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.

Graphical abstract: Total syntheses of mitragynine, paynantheine and speciogynine via an enantioselective thiourea-catalysed Pictet–Spengler reaction

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Article information


Submitted
27 Sep 2012
Accepted
05 Nov 2012
First published
13 Nov 2012

Chem. Commun., 2012,48, 12243-12245
Article type
Communication

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

I. P. Kerschgens, E. Claveau, M. J. Wanner, S. Ingemann, J. H. van Maarseveen and H. Hiemstra, Chem. Commun., 2012, 48, 12243
DOI: 10.1039/C2CC37023A

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