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Type: Artigo de periódico
Title: The asymmetric total synthesis of (+)- and (-)-trypargine via Noyori asymmetric transfer hydrogenation
Author: Pilli, Ronaldo A.
Rodrigues Jr, Manoel Trindade
Abstract: A concise and efficient total synhesis of (+)- and (-)-trypargine (6 steps and 38% overall yield), a 1-substituted β-carboline guanidine alkaloid isolated from the skin of the African frog K. senegalensis, was developed based on the construction of the β-carboline moiety via Bischler-Napieralski reaction and the enantioselective reduction of the dihydro-β-carboline intermediate via an asymmetric transfer hydrogenation reaction using Noyori's protocol.
Uma síntese total e eficiente da (+) e (-)-tripargina, alcalóide β-carbolínico isolado da pele da rã africana K. Senegalensis, foi realizada em 6 etapas e 38% de rendimento global, a partir da triptamina, tendo como base a construção do sistema β-carbolínico via reação de Bischler-Napieralski e a redução enantiosseletiva do intermediário diidro-β-carbolínico via reação de transferência de hidrogênio assimétrica usando o protocolo de Noyori.
Subject: trypargine
tetrahydro β-carboline alkaloid
Bischler-Napieralski reaction
Noyori asymmetric transfer hydrogenation
Editor: Sociedade Brasileira de Química
Rights: aberto
Identifier DOI: 10.1590/S0103-50532009000800007
Date Issue: 1-Jan-2009
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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