Document Detail


Total syntheses of mitragynine, paynantheine and speciogynine via an enantioselective thiourea-catalysed Pictet-Spengler reaction.
MedLine Citation:
PMID:  23150886     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Isabel P Kerschgens; Elise Claveau; Martin J Wanner; Steen Ingemann; Jan H van Maarseveen; Henk Hiemstra
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-11-13
Journal Detail:
Title:  Chemical communications (Cambridge, England)     Volume:  -     ISSN:  1364-548X     ISO Abbreviation:  Chem. Commun. (Camb.)     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-14     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9610838     Medline TA:  Chem Commun (Camb)     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Van 't Hoff Institute for Molecular Sciences, Science Park 904, 1098XH Amsterdam, The Netherlands. j.h.vanmaarseveen@uva.nl h.hiemstra@uva.nl.
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