Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 10, Issue 13, Pages 3286-3300Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200305581
Keywords
alkaloids; asymmetric synthesis; cyclization; heterocycles; metathesis
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The double ring-closing metathesis reaction of nitrogen-containing tetraenes was studied. The selectivity of the fused/dumbbell-type products can be controlled by the electronic/steric effects of the substituents attached to the C = C bonds and the s-cis/s-trans conformational ratios of the substrates. This methodology has also been successfully applied to the enantioselective synthesis of four stereoisomers of lupinine and their derivatives.
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