complanadine-b and lycodine

complanadine-b has been researched along with lycodine* in 2 studies

Other Studies

2 other study(ies) available for complanadine-b and lycodine

Article	Year
Competent Route to Unsymmetric Dimer Architectures: Total Syntheses of (-)-Lycodine and (-)-Complanadines A and B, and Evaluation of Their Neurite Outgrowth Activities. Chemistry (Weinheim an der Bergstrasse, Germany), 2017, Jan-18, Volume: 23, Issue:4 Valuable synthetic routes to the Lycopodium alkaloid lycodine (1) and its unsymmetric dimers, complanadines A (4) and B (5), have been developed. Regioselective construction of the bicyclo[3.3.1]nonane core structure of lycodine was achieved by a remote functionality-controlled Diels-Alder reaction and subsequent intramolecular Mizoroki-Heck reaction. A key coupling reaction of the lycodine units, pyridine N-oxide (66) and aryl bromide (65), through C-H arylation at the C1 position of 66 provided the unsymmetric dimer structure at a late stage of the synthesis. This strategy greatly simplified the construction of the dimeric architecture and functionalization. Complanadines A (4) and B (5) were synthesized by adjusting the oxidation level of the bipyridine mono-N-oxide (67). The diverse utility of this common intermediate (67) suggests a possible biosynthetic pathway of complanadines in Nature. Both enantiomers of lycodine (1) and complanadines A (4) and B (5) were prepared in sufficient quantities for biological evaluation. The effect on neuron differentiation of PC-12 cells upon treatment with culture medium, in which human astrocytoma cells had been cultured in the presence of 1, 4, or 5 was evaluated. Topics: Alkaloids; Animals; Cell Line, Tumor; Crystallography, X-Ray; Cycloaddition Reaction; Dimerization; Heterocyclic Compounds, 4 or More Rings; Humans; Molecular Conformation; Neuronal Outgrowth; Oxidation-Reduction; PC12 Cells; Pyridines; Rats; Stereoisomerism	2017
A model system for the synthesis of complanadine alkaloids by "diverted Kondrat'eva" oxazole-olefin cycloaddition. The Journal of organic chemistry, 2013, Jun-21, Volume: 78, Issue:12 A synthetic approach to complanadine alkaloids is described which employs a Kondrat'eva reaction to construct the pyridine rings. The viability of this approach is demonstrated by its application to a model substrate accessed from unfunctionalized decalin. The key transformation affords the desired tetracyclic architecture with unprecedented incorporation of substituents on the pyridine ring, implicating the oxazole α-hydroxy group as an active participant in the cycloadduct fragmentation process. Topics: Alkaloids; Alkenes; Cycloaddition Reaction; Heterocyclic Compounds, 4 or More Rings; Molecular Structure; Naphthalenes; Oxazoles; Pyridines	2013

Article

Year

Competent Route to Unsymmetric Dimer Architectures: Total Syntheses of (-)-Lycodine and (-)-Complanadines A and B, and Evaluation of Their Neurite Outgrowth Activities.

Chemistry (Weinheim an der Bergstrasse, Germany), 2017, Jan-18, Volume: 23, Issue:4

Valuable synthetic routes to the Lycopodium alkaloid lycodine (1) and its unsymmetric dimers, complanadines A (4) and B (5), have been developed. Regioselective construction of the bicyclo[3.3.1]nonane core structure of lycodine was achieved by a remote functionality-controlled Diels-Alder reaction and subsequent intramolecular Mizoroki-Heck reaction. A key coupling reaction of the lycodine units, pyridine N-oxide (66) and aryl bromide (65), through C-H arylation at the C1 position of 66 provided the unsymmetric dimer structure at a late stage of the synthesis. This strategy greatly simplified the construction of the dimeric architecture and functionalization. Complanadines A (4) and B (5) were synthesized by adjusting the oxidation level of the bipyridine mono-N-oxide (67). The diverse utility of this common intermediate (67) suggests a possible biosynthetic pathway of complanadines in Nature. Both enantiomers of lycodine (1) and complanadines A (4) and B (5) were prepared in sufficient quantities for biological evaluation. The effect on neuron differentiation of PC-12 cells upon treatment with culture medium, in which human astrocytoma cells had been cultured in the presence of 1, 4, or 5 was evaluated.

Topics: Alkaloids; Animals; Cell Line, Tumor; Crystallography, X-Ray; Cycloaddition Reaction; Dimerization; Heterocyclic Compounds, 4 or More Rings; Humans; Molecular Conformation; Neuronal Outgrowth; Oxidation-Reduction; PC12 Cells; Pyridines; Rats; Stereoisomerism

2017

A model system for the synthesis of complanadine alkaloids by "diverted Kondrat'eva" oxazole-olefin cycloaddition.

The Journal of organic chemistry, 2013, Jun-21, Volume: 78, Issue:12

A synthetic approach to complanadine alkaloids is described which employs a Kondrat'eva reaction to construct the pyridine rings. The viability of this approach is demonstrated by its application to a model substrate accessed from unfunctionalized decalin. The key transformation affords the desired tetracyclic architecture with unprecedented incorporation of substituents on the pyridine ring, implicating the oxazole α-hydroxy group as an active participant in the cycloadduct fragmentation process.

Topics: Alkaloids; Alkenes; Cycloaddition Reaction; Heterocyclic Compounds, 4 or More Rings; Molecular Structure; Naphthalenes; Oxazoles; Pyridines

2013