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Total synthesis of the antimalarial naphthylisoquinoline alkaloid 5-epi-4′-O-demethylancistrobertsonine C by asymmetric Suzuki cross-coupling
- Source :
-
Tetrahedron . Jun2008, Vol. 64 Issue 23, p5563-5568. 6p. - Publication Year :
- 2008
-
Abstract
- Abstract: 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. [Copyright &y& Elsevier]
- Subjects :
- *ORGANONITROGEN compounds
*NITROGEN compounds
*ORGANIC compounds
*ORGANIC chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 64
- Issue :
- 23
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 32050003
- Full Text :
- https://doi.org/10.1016/j.tet.2008.03.087