The Total Syntheses of Isoquinoline Alkaloids

Kametani, Tetsuji

doi:10.1002/9780470129661.ch1

Cited by 16 publications

(3 citation statements)

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“…Erysodienone 12 , morphine 13 , and emetine 14 are typical members of the isoquinoline alkaloid family (Figure ). The solutions proposed for the two first molecules correspond to known convergent syntheses , but not for the last one . Though synthesis of channaine 15 has yet to be described, this example is interesting because the set of bond disconnections shows that 15 is probably a dimer of N -demethylmesembrenone .…”

Section: Resultsmentioning

confidence: 98%

“…The solutions proposed for the two first molecules correspond to known convergent syntheses 49,50 but not for the last one. 51 Though synthesis of channaine 15 has yet to be described, this example is interesting because the set of bond disconnections shows that 15 is probably a dimer of N-demethylmesembrenone. 52 It should be noted that potential symmetry is not easily recognized at a glance from the two channaine formulas 15 and 15′ depicted in Figure 16.…”

Section: Resultsmentioning

confidence: 99%

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Maximum Symmetrical Split of Molecular Graphs. Application to Organic Synthesis Design

Vismara

Tognetti

2005

J. Chem. Inf. Model.

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Whereas the potential symmetry of a molecule may be a feature of importance in synthesis design, this one is often difficult to detect visually in the structural formula. In the present article, we describe an efficient algorithm for the perception of this molecular property. We have addressed this problem in terms of graph theory and defined it as the Maximum Symmetrical Split of a molecular graph. A solution is obtained by deleting in such a graph a minimum number of edges and vertices so that the resulting subgraph consists of exactly two isomorphic connected components that correspond to a pair of synthetically equivalent synthons. In view to reduce the search space of the problem, we have based our algorithm on CSP techniques. In this study, we have found that the maximum symmetrical split is an original kind of Constraint Satisfaction Problem. The algorithm has been implemented into the RESYN_Assistant system, and its performance has been tested on a set of varied molecules which were the targets of previously published synthetic studies. The results show that potential symmetry is perceived quickly and efficiently by the program. The graphical display of this perception information may help a chemist to design reflexive or highly convergent syntheses.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Maximum Symmetrical Split of Molecular Graphs. Application to Organic Synthesis Design

Vismara

Tognetti

2005

J. Chem. Inf. Model.

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“…The slight differences in the chemical shifts may be contributed to the different solvents used for the NMR measurement. The optical rotation of all known isolated compounds were found to be (-ve) thus corresponding to β configuration [7]. Therefore, based on biogenetic reasoning, the configuration at C-6a for (-)- N -methylguattescidine is deduced to be β.…”

Section: Resultsmentioning

confidence: 99%

Alkaloids from Fissistigma latifolium (Dunal) Merr.

et al. 2010

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A phytochemical study of the bark of Fissistigma latifolium (Annonaceae) yielded a new aporphine alkaloid, (-)-N-methylguattescidine (1), and eight known alkaloids: liriodenine (2), oxoxylopine (3), (-)-asimilobine (4), dimethyltryptamine (5), (-)-remerine (6), (-)-anonaine (7), columbamine (8) and lysicamine (9). The compounds were isolated using various chromatographic methods and structural elucidation was accomplished by means of spectroscopic methods, notably 1D-NMR (1H, 13C, DEPT), 2D-NMR (COSY, HMQC, HMBC), UV, IR and MS.

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Selective Halogen‐Lithium Exchange Reactions of 2‐(2′‐Halophenyl)Ethyl Halides: Synthesis of 4,5‐Methylenedioxybenzocyclobutene and 1‐Phenyl‐3,4‐Dihydro‐6,7‐Methylenedioxyisoquinoline

2003

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Selective halogen‐lithium exchange reactions of 2‐(2′‐halophenyl)ethyl halides: synthesis of 4,5‐methylenedioxybenzocyclobutene and 1‐phenyl‐3,4‐dihydro‐6,7‐methylenedioxyisoquinoline reactant: 10.0 g (37.9 mmol) of 2‐(2′‐bromo‐4′,5′‐methylenedioxyphenyl)ethyl chloride product: 4,5‐methylenedioxybenzocyclobutene product: 1‐Phenyl‐3,4‐dihydro‐6,7‐methylenedioxyisoquinoline intermediate: 2‐(3′,4′‐methylenedioxyphenyl)ethanol intermediate: 2‐(2′‐bromo‐4′,5′‐methylenedioxyphenyl)ethanol

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The Total Syntheses of Isoquinoline Alkaloids

Cited by 16 publications

References 523 publications

Maximum Symmetrical Split of Molecular Graphs. Application to Organic Synthesis Design

Maximum Symmetrical Split of Molecular Graphs. Application to Organic Synthesis Design

Alkaloids from Fissistigma latifolium (Dunal) Merr.

Selective Halogen‐Lithium Exchange Reactions of 2‐(2′‐Halophenyl)Ethyl Halides: Synthesis of 4,5‐Methylenedioxybenzocyclobutene and 1‐Phenyl‐3,4‐Dihydro‐6,7‐Methylenedioxyisoquinoline

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