Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 6, Pages 793-796Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200801175
Keywords
Alkaloids; Asymmetric catalysis; Heck reaction; Radical reactions; Cyclization
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Funding
- Katholieke Universiteit Leuven
- FWO (Fund for Scientific Research - Flanders, Belgium)
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A short enantioselective approach towards the alkaloid (-)-aphanorphine and its substituted analogues is described. The enantiomerically pure starting material for the synthesis was obtained by asymmetric hydrogenation in the presence of the Rh-(S)-PipPhos complex. Microwave-assisted Heck cyclization selectively provided the seven-membered 3-benzazepine ring. Further, the assembly of the tricyclic core of the alkaloid was accomplished by intramolecular radical cyclization. The X-ray structure confirming the absolute configuration of the obtained products is described. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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