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Double Ring‐Closing Metathesis Reaction of Nitrogen‐Containing Tetraenes: Efficient Construction of Bicyclic Alkaloid Skeletons and Synthetic Application to Four Stereoisomers of Lupinine and Their Derivatives
Author(s) -
Ma Shengming,
Ni Bukuo
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200305581
Subject(s) - steric effects , chemistry , metathesis , ring closing metathesis , enantioselective synthesis , bicyclic molecule , salt metathesis reaction , stereochemistry , alkaloid , ring (chemistry) , selectivity , organic chemistry , catalysis , polymerization , polymer
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 CC 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.