ChemInform Abstract: The Formation of a Novel Pd/C—Ethylenediamine Complex Catalyst: Chemoselective Hydrogenation Without Deprotection of the O‐Benzyl and N‐Cbz Groups.

Sajiki, Hironao; Hattori, Katsumi; Hirota, Kosaku

doi:10.1002/chin.199914057

Cited by 6 publications

(7 citation statements)

References 1 publication

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“…The latter were hydrogenated with poisoned Pd/C 28 using a previously published procedure 29 to obtain crude mixtures resulting from nitro group reduction and 5–20% ring opening. As a result of instability on silica gel, the reduced product mixtures were used directly without purification.…”

Section: Synthesismentioning

confidence: 99%

Enantiomeric Propanolamines as selectiveN-Methyl-d-aspartate 2B Receptor Antagonists

et al. 2008

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Enantiomeric propanolamines have been identified as a new class of NR2B-selective NMDA receptor antagonists. The most effective agents are biaryl structures, synthesized in six steps with overall yields ranging from 11–64%. The compounds are potent and selective inhibitors of NR2B-containing recombinant NMDA receptors with IC50 values between 30–100 nM. Potency is strongly controlled by substitution on both rings and the centrally located amine nitrogen. SAR analysis suggests that well-balanced polarity and chain-length factors provide the greatest inhibitory potency. Structural comparisons based on 3D shape analysis and electrostatic complementarity support this conclusion. The antagonists are neuroprotective in both in vitro and in vivo models of ischemic cell death. In addition, some compounds exhibit anticonvulsant properties. Unlike earlier generation NMDA receptor antagonists and some NR2B-selective antagonists, the present series of propanolamines does not cause increased locomotion in rodents. Thus, the NR2B-selective antagonists exhibit a range of therapeutically interesting properties.

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Section: Synthesismentioning

confidence: 99%

Enantiomeric Propanolamines as selectiveN-Methyl-d-aspartate 2B Receptor Antagonists

et al. 2008

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“…Accordingly, aldehyde 29 was allylated by following the Barbier-type protocol to give 32a and 32b in 27 and 58% yield, respectively. The minor isomer 32a was shown to undergo terminal olefin cross-metathesis [107][108][109] with 1-heptene and subsequent hydrogenation [110] to lead to exclusive production of 30a, as confirmed by 1 H NMR spectroscopy. Meanwhile, another diastereomer 32b was subjected to derivatization with (R)-and (S)α-methoxy-α-(trifluoromethyl)phenylacetyl chloride (MTPACl) to convert into the corresponding (S)-and (R)-MTPA esters 33, respectively (Figure 9).…”

Section: Syntheses Of Batzellasidesmentioning

confidence: 77%

Evolution of the Total Syntheses of Batzellasides the First Marine Piperidine Iminosugar

Sengoku

Wierzejska

Takahashi

et al. 2013

Natural Product Communications

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Batzellasides A-C are C-alkylated piperidine iminosugars isolated from a sponge, Batzella sp. The first total synthesis of (+)-batzellaside B was achieved by employing a chiral pool approach starting from L-arabinose for the construction of a piperidine ring system. Subsequently, a practical second-generation synthesis was developed by utilizing a Sharpless asymmetric dihydroxylation for the preparation of the common piperidine intermediate elaborated in the firstgeneration synthesis. The overall yield of batzellaside B was improved to 3.3% by introducing the exocyclic C8 stereocenter via facial selective hydride addition to a linear ketone. These syntheses allowed for the determination of the absolute stereochemistry of this natural product as well as for providing precious samples, which would pave the way for further biological studies.

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“…In addition, when the reaction was performed on the benchtop with only 5 mol % of (Co(III) L ) and with pivalic acid as the additive, the product was obtained with only a slight reduction in the yield to 60%. Alkene hydrogenation 31 to provide 14 was followed by amide N -nitrosylation 32 , saponification and benzyl group cleavage to furnish alcohol 15 in excellent overall yield.…”

Section: Resultsmentioning

confidence: 99%

Selective and synergistic cobalt(iii)-catalysed three-component C–H bond addition to dienes and aldehydes

et al. 2018

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Two-component C–H bond additions to a large variety of coupling partners have been developed with applications towards materials, natural product and drug synthesis. Sequential three-component C–H bond addition across two different coupling partners potentially enables the convergent synthesis of complex molecular scaffolds from simple precursors. Here, we report three-component Co(III)-catalyzed C–H bond additions to dienes and aldehydes that proceeds with high regio- and stereoselectivity resulting in two new carbon-carbon σ-bonds and from four to six new stereocenters. The reaction relies on the synergistic reactivity of the diene and aldehyde with neither undergoing C–H bond addition alone. A detailed mechanism is supported by X-ray structural characterization of a Co(III)-allyl intermediate, observed transfer of stereochemical information, and kinetic isotope studies. The applicability of the method to biologically relevant molecules is exemplified by the rapid synthesis of the western fragment of the complex ionophore antibiotic lasalocid A.

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ChemInform Abstract: The Formation of a Novel Pd/C—Ethylenediamine Complex Catalyst: Chemoselective Hydrogenation Without Deprotection of the O‐Benzyl and N‐Cbz Groups.

Cited by 6 publications

References 1 publication

Enantiomeric Propanolamines as selectiveN-Methyl-d-aspartate 2B Receptor Antagonists

Enantiomeric Propanolamines as selectiveN-Methyl-d-aspartate 2B Receptor Antagonists

Evolution of the Total Syntheses of Batzellasides the First Marine Piperidine Iminosugar

Selective and synergistic cobalt(iii)-catalysed three-component C–H bond addition to dienes and aldehydes

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