Total synthesis of the antimalarial naphthylisoquinoline alkaloid 5- epi-4′- O-demethylancistrobertsonine C by asymmetric Suzuki cross-coupling

The first total synthesis of the antimalarial naphthylisoquinoline alkaloid 5- epi-4′- O-demethylancistrobertsonine C ( 1a) and its—as yet unnatural—atropo-diastereomer, 1b, is described. The key step of the synthesis is the construction of the rotationally hindered and thus stereogenic biaryl axis,...

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Veröffentlicht in:Tetrahedron 2008-06, Vol.64 (23), p.5563-5568
Hauptverfasser: Bringmann, Gerhard, Rüdenauer, Stefan, Bruhn, Torsten, Benson, Lauren, Brun, Reto
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container_issue 23
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container_title Tetrahedron
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creator Bringmann, Gerhard
Rüdenauer, Stefan
Bruhn, Torsten
Benson, Lauren
Brun, Reto
description The first total synthesis of the antimalarial naphthylisoquinoline alkaloid 5- epi-4′- O-demethylancistrobertsonine C ( 1a) and its—as yet unnatural—atropo-diastereomer, 1b, is described. The key step of the synthesis is the construction of the rotationally hindered and thus stereogenic biaryl axis, which was built up by a Suzuki reaction. The use of chiral ligands in the palladium-catalyzed cross-coupling permitted to increase the low internal asymmetric induction up to a diastereomeric ratio of 74:26. The assignment of the axial configurations of the atropo-diastereomers was achieved by 2D NMR experiments and corroborated by quantum chemical CD calculations. [Display omitted]
doi_str_mv 10.1016/j.tet.2008.03.087
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subjects Absolute configuration
Chiral ligands
Naphthylisoquinoline alkaloids
Quantum chemical CD calculations
Suzuki cross-coupling
title Total synthesis of the antimalarial naphthylisoquinoline alkaloid 5- epi-4′- O-demethylancistrobertsonine C by asymmetric Suzuki cross-coupling
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