The enantioselective total synthesis of alkaloid (−)-galipeine
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Quinoline
Derivative (finance)
Asymmetric hydrogenation
Asymmetric hydrogenation
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Derivative (finance)
Ethyl acetoacetate
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Two ω-mercaptoalkoxy quinoline compounds:6-(ω-mercaptodecoxy)-quinoline and 2-(ω-mercaptodecoxy)-4-methyl-quinoline were succesfully synthesized by reacting quinoline with 1,10- dibromodecane and thiourea in alkaline solution. The intermediates and products were characterized by IR, 1H NMR and MS.
Quinoline
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The coumarin imperatorin and the quinoline alkaloids kokusagine, japonin, and O-methylbalfourodinium salt were isolated from the leaves and from the stems of Orixa japonica Thunb. A new ketonic quinoline alkaloid, orixinone [2,4-dimethoxy-7,8-methylenedioxy-3-(3-methyl-2-oxobutyl)quinoline], was identified.
Quinoline
Imperatorin
Sanguinarine
Methylenedioxy
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Abstract An enantioselective asymmetric total synthesis of (+)‐vittatalactone has been accomplished employing enzymatic desymmetrization approach to create two methyl chiral centres. Other key steps involved are Wittig reaction, Evan's asymmetric alkylation, hydroboration, TEMPO‐BAIB‐mediated selective oxidation of 1,3‐diol and lactonization mediated by p ‐toluenesulfonyl chloride. The total synthesis was achieved by a linear synthetic sequence with an overall yield of 11.8 %.
Desymmetrization
Wittig reaction
Hydroboration
Aldol reaction
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An enantioselective hydrogenation of N-substituted diarylmethanimines under mild conditions has been first realized by using an iridium catalyst with a chiral f-spiroPhos ligand. This method provides an efficient access to the asymmetric synthesis of a variety of chiral diarylmethylamines and their derivatives with excellent enantioselectivities (up to 99.4% ee) and high turnover numbers (TON up to 4000).
Asymmetric hydrogenation
Chiral ligand
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Quinoline
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A late-stage resolution of the meso-3a,3a′-bispyrrolidinoindoline unit of rac-7 in a catalytic asymmetric transformation earmarks the remarkably short, ten-step, total syntheses of hodgkinsine and hodgkinsine B. The enantioselective total synthesis of hodgkinsine B establishes the relative and absolute configuration of this trispyrrolidinoindoline alkaloid.
Absolute Configuration
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Aldol reaction
Formal synthesis
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Two alkaloids, megistoquinone I (1) and megistoquinone II (2), were isolated from the bark of Sarcomelicope megistophylla. Their structures have been elucidated on the basis of MS and NMR data. Both belong to quinoline alkaloid series and should be considered as oxidation products of a furo[2,3-b]quinoline precursor. The two alkaloids showed antibacterial properties with minimum inhibitory concentration (MIC) ranging from 2.35 to 5.25 mg/ml for 1 and 0.73 to 1.23 mg/ml for 2.
Quinoline
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This paper describes an efficient hydrogenation procedure to afford enantioenriched hydrogenated quinoline derivatives. The same catalyst is also capable for the hydrogenation of quinoline N-oxide, although the conversion and enantioselectivity still need to be improved.
Quinoline
Asymmetric hydrogenation
Noyori asymmetric hydrogenation
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