Literature DB >> 23150886

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

Isabel P Kerschgens1, Elise Claveau, Martin J Wanner, Steen Ingemann, Jan H van Maarseveen, Henk Hiemstra.   

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.

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Year:  2012        PMID: 23150886     DOI: 10.1039/c2cc37023a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  4 in total

Review 1.  Synthesis of indole derivatives as prevalent moieties present in selected alkaloids.

Authors:  Majid M Heravi; Zahra Amiri; Kosar Kafshdarzadeh; Vahideh Zadsirjan
Journal:  RSC Adv       Date:  2021-10-15       Impact factor: 4.036

2.  Sequential Sonagashira and Larock indole synthesis reactions in a general strategy to prepare biologically active β-carboline-containing alkaloids.

Authors:  Xiaohong Pan; Thomas D Bannister
Journal:  Org Lett       Date:  2014-11-13       Impact factor: 6.005

Review 3.  Natural Products for the Treatment of Pain: Chemistry and Pharmacology of Salvinorin A, Mitragynine, and Collybolide.

Authors:  Soumen Chakraborty; Susruta Majumdar
Journal:  Biochemistry       Date:  2020-09-22       Impact factor: 3.162

Review 4.  The Pictet-Spengler Reaction Updates Its Habits.

Authors:  Andrea Calcaterra; Laura Mangiardi; Giuliano Delle Monache; Deborah Quaglio; Silvia Balducci; Simone Berardozzi; Antonia Iazzetti; Roberta Franzini; Bruno Botta; Francesca Ghirga
Journal:  Molecules       Date:  2020-01-19       Impact factor: 4.411

  4 in total

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