Synthesis of Homoesermethole.

Murayama, Masao

doi:10.1248/cpb.6.200

Cited by 7 publications

(5 citation statements)

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“…The open ring compounds 5 and 6 ( Table 1) were obtained by reaction of the ketones 5b and 6b with NaBH 4 and subsequent conversion with CDI (Scheme 4). For the synthesis of compound 6b, the pyridine N-oxide 6a was prepared from 3-acetylpyridine and ethylene glycol [11] and subsequent Noxidation of the ketal using benzonitrile/H 2 O 2 (pH: [8][9] according to the method of Payne et al [12] . O-Methylation of the N-oxide using dimethyl sulfate and subsequent reaction of the crude product with KCN under alkaline conditions and exclusion of oxygen afforded the nitrile 6c.…”

Section: Methodsmentioning

confidence: 99%

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1-Imidazolylcarbonyloxy-substituted Tetrahydroquinolines and Pyridines: Synthesis and Evaluation of P450 TxA2 Inhibition

Hartmann

Frotscher

1999

Arch. Pharm. Pharm. Med. Chem.

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The title compounds are derived from our model describing structural requirements for strong P450 TxA2 inhibition [1]. In the present paper the syntheses of the 1‐imidazolylcarbonyloxy‐substituted tetrahydroquinolines 1, 3, and 4, tetrahydro‐naphthalene 2 and 3‐ethylpyridines 5 and 6 are described. Using our P450 TxA2 inhibition assay, 1—6 were tested for enzyme inhibitory activity. Compound 1 (5‐(1‐imidazolylcarbonyloxy)‐5,6,7,8‐tetrahydroquinoline) turned out to be the most active derivative showing a potency similar to the reference compound dazoxiben (IC50 values 1.6 and 1.1 μM).

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Section: Methodsmentioning

confidence: 99%

“…5.0 g (33.1 mmol) 3-(1-ethylenedioxyethyl)pyridine [11] is dissolved in 9 ml methanol and 3.4 g (33.1 mmol) benzonitrile and 5.1 g finely powdered H2O2-urea-adduct (33% H2O2, corresoponding to 50 mmol) are added. The temperature of the mixture decreases strongly.…”

Section: -(1-ethylenedioxyethyl)pyridine N-oxide 6dmentioning

confidence: 99%

1-Imidazolylcarbonyloxy-substituted Tetrahydroquinolines and Pyridines: Synthesis and Evaluation of P450 TxA2 Inhibition

Hartmann

Frotscher

1999

Arch. Pharm. Pharm. Med. Chem.

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“…[54] The presence of a quaternary center at C3 is key to the formation of the cyclic tryptamine tautomer in this instance, as N a -methyl-3-(2aminoethyl)oxindole is reduced under these conditions to N a -methyltryptamine. [55] In a more biomimetic approach, substituted tryptamines have been dimerized in vitro with various oxidants. In a seminal contribution to this area, the magnesium salt of N bmethyltryptamine 24 was used by Scott and co-workers to procure (AE )-chimonanthine, presumably via the radicalcoupling products, diindolenines 26 and 27 (path A in Scheme 5).…”

Section: Construction Of Contiguous Quaternary Carbonmentioning

confidence: 99%

Total Synthesis of Complex Cyclotryptamine Alkaloids: Stereocontrolled Construction of Quaternary Carbon Stereocenters

2007

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Our ability to access the more complex members of the cyclotryptamine family of alkaloids, and to exploit their disparate biological activities, is limited by the synthetic challenge posed by their oligomeric, polyindoline structures. A recurring structural theme within these molecules is the presence of multiple quaternary stereocenters in close proximity to one another. Over the last decade, we have developed a set of transformations that allow rapid access to polyindolines, a number of which exploit the ability of catalytic levels of palladium to orchestrate carbon-carbon bond formation with impressive levels of regio- and stereocontrol. This review tells the story behind the development of this toolbox of synthetic methods, and their validation through the total synthesis of a number of structurally complex cyclotryptamine alkaloids. It also highlights an aspect of asymmetric catalysis that has received little attention, the ability of catalytic asymmetric reactions to selectively elaborate complex, polyfunctional molecules.

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“…for C15H14N4010: C,43.91;H,3.44;N,13.66. Found: C,44.15;11,3.14;N,14.26. This conversion to 8 was increased by use of higher molar ratios of formaldehyde to 6. At 185' (2.5 hours) in a 300 ml.…”

Section: -Hydroxymethyl-2~4-pyridyl)-l3-dioxolane (8)mentioning

confidence: 99%

The hydroxyacetylpiperidines and their N‐benzyl derivatives. The 2‐hydroxymethyl‐2‐piperidyl‐ and 2‐hydroxymethyl‐2‐pyridyl‐1,3‐dioxolanes

Nielsen

Platt

1969

Journal of Heterocyclic Chem

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The hydroxyacetylpiperidines, their ethylene ketals, and the N‐benzyl derivatives of these new piperidines have been synthesized. Methylolation of 2‐(2‐ and 4‐pyridyl)‐1,3‐dioxolanes by heating with paraformaldehyde at 185° led to 2‐hydroxymethyl‐2‐(2‐ and 4‐pyridyl)‐i,3‐dioxolanes (7,8, respectively). 2‐Hydroxymethyl‐2‐(3‐pyridyl)‐1,3‐dioxolane (13) was obtained by reaction of 2‐bromomethyl‐2‐(3‐pyridyl)‐1,3‐dioxolane with aqueous sodium hydroxide at 190°. Hydrogenation of these pyridine ketals with rhodium‐charcoal catalyst produced the corresponding piperidine ketals (16,17,18). Acid hydrolysis of the piperidine ketals and their N‐benzyl derivatives led to the hydroxyacetylpiperidines (1,2,3) and their N‐benzyl derivatives (25,26,27). The N‐benzylhydroxyacetylpiperidines undergo rapid hydrogenolysis with palladium‐charcoal catalyst to produce the hydroxyacetylpiperidines. Further hydrogenation produces the piperidyl‐1,2‐ethanediols. The hydroxyacetylpiperidines are somewhat unstable, hygroscopic substances which polymerize with dehydration on standing; in solution they are relatively stable. Their N‐benzyl, ketal, and hydrochloride salt derivatives, on the other hand, represent stable, synthetically useful intermediates from which the reactive trifunctional hydroxyacetylpiperidines may readily be prepared.

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Synthesis of Homoesermethole.

Cited by 7 publications

References 0 publications

1-Imidazolylcarbonyloxy-substituted Tetrahydroquinolines and Pyridines: Synthesis and Evaluation of P450 TxA2 Inhibition

1-Imidazolylcarbonyloxy-substituted Tetrahydroquinolines and Pyridines: Synthesis and Evaluation of P450 TxA2 Inhibition

Total Synthesis of Complex Cyclotryptamine Alkaloids: Stereocontrolled Construction of Quaternary Carbon Stereocenters

The hydroxyacetylpiperidines and their N‐benzyl derivatives. The 2‐hydroxymethyl‐2‐piperidyl‐ and 2‐hydroxymethyl‐2‐pyridyl‐1,3‐dioxolanes

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