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.
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[double bond]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.
Ma
Shengming
S
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China. masm@mail.sioc.ac.cn
Ni
Bukuo
B
D000470:Alkaloids / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D003500:Cyclization; D008958:Models, Molecular; D019906:Nuclear Magnetic Resonance, Biomolecular; D013034:Sparteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism; D000093843:Quinolizidine Alkaloids
D000470:Alkaloids; D000475:Alkenes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D013034:Sparteine; C015971:lupinine; D000093843:Quinolizidine Alkaloids