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 | Zendy

Ma Shengming | Zendy; Ni Bukuo | Zendy

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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.

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