Oxidative decarboxylation of .alpha.-hydroxycarboxylic acids with N-iodosuccinimide

Beebe, Thomas R.; Adkins, R. L.; Belcher, A. I.; Choy, T.; Fuller, Anshuman; Morgan, V. L.; SENCHEREY, B. B.; Russell, L J; Yates, S. W.

doi:10.1021/jo00136a041

Cited by 20 publications

(3 citation statements)

References 2 publications

(4 reference statements)

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“…The mechanism by which this decomposition happens is as of yet unknown, but it is worth noting that other groups have reported the decarboxylation of α-hydroxy carboxylic acids through chemical and enzymatic methods. − Although 100 °C is acknowledged to not be a biologically relevant temperature, this type of degradation warrants further investigation because it could have potential implications for chemical stability of other ALLINIs as the t -butoxy acetic acid side chain is an important pharmacophore for all potent ALLINIs.…”

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confidence: 99%

An Isoquinoline Scaffold as a Novel Class of Allosteric HIV-1 Integrase Inhibitors

Wilson

Koneru

Rebensburg

et al. 2019

ACS Med. Chem. Lett.

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Allosteric HIV-1 integrase inhibitors (ALLINIs) are a new class of potential antiretroviral therapies with a unique mechanism of action and drug resistance profile. To further extend this class of inhibitors via a scaffold hopping approach, we have synthesized a series of analogues possessing an isoquinoline ring system. Lead compound 6l binds in the v-shaped pocket at the IN dimer interface and is highly selective for promoting higher-order multimerization of inactive IN over inhibiting IN-LEDGF/p75 binding. Importantly, 6l potently inhibited HIV-1 NL4−3 (A128T IN), which confers marked resistance to archetypal quinoline-based ALLINIs. Thermal degradation studies indicated that at elevated temperatures the acetic acid side chain of specific isoquinoline derivatives undergo decarboxylation reactions. This reactivity has implications for the synthesis of various ALLINI analogues.

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confidence: 99%

An Isoquinoline Scaffold as a Novel Class of Allosteric HIV-1 Integrase Inhibitors

Wilson

Koneru

Rebensburg

et al. 2019

ACS Med. Chem. Lett.

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“…All attempts to further improve this procedure or to effect the same transformation using chemical oxidants (i.e., NIS or NBS) [32] largely met with failure. While, in principle, ent-30 could be accessed from the same starting material simply by reversing the order of the alkylation steps (i.e., ethylation prior to methylation), such a process resulted in significantly reduced enolate reactivity towards the second electrophilic partner and poorer levels of diastereoselection.…”

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confidence: 99%

Total Synthesis of Berkelic Acid

Snaddon

Buchgraber

Schulthoff

et al. 2010

Chemistry A European J

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A productive total synthesis of both enantiomers of berkelic acid (1) is outlined that takes the structure revision of this bioactive fungal metabolite previously proposed by our group into account. The successful route relies on a fully optimized triple-deprotection/1,4-addition/spiroacetalization cascade reaction sequence, which delivers the tetracyclic core 32 of the target as a single isomer in excellent yield. The required cyclization precursor 31 is assembled from the polysubstituted benzaldehyde derivative 20 and methyl ketone 25 by an aldol condensation, in which the acetyl residue in 20 transforms from a passive protecting group into an active participant. Access to fragment 25 takes advantage of the Collum-Godenschwager variant of the ester enolate Claisen rearrangement, which clearly surpasses the classical Ireland-Claisen procedure in terms of diastereoselectivity. Although it is possible to elaborate 32 into the target without any additional manipulations of protecting groups, a short detour consisting in the conversion of the phenolic -OH into the corresponding TBS-ether is beneficial. It tempers the sensitivity of the compound toward oxidation and hence improves the efficiency and reliability of the final stages. Orthogonal ester groups for the benzoate and the aliphatic carboxylate terminus of the side chain secure an efficient liberation of free berkelic acid in the final step of the route.

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“…Oxidative decarboxylation of a-hydroxy acids to aldehydes or ketones can be achieved with various oxidizing agents, such as chromic acid, 3 sodium bismuthate, 4 lead tetraacetate, 5 nickel peroxide, 6 periodate, 7 and Niodosuccinimide 8 but, in the absence of the a-hydroxy group, there are only few systems available for decarboxylation of simple carboxylic acids to aldehydes and ketones, such as tetrabutylammonium periodate, 9 sodium periodate in combination with polystyrene-bound Mn(T4PyP) or iron and manganese tetraphenylporphyrins. 10 In connection with oxidative decarboxylation of aamino acids, it was reported the lead tetraacetate oxidation of their N-acyl derivatives gave N-acylimines which were hydrolyzed to the corresponding aldehydes.…”

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confidence: 99%

Oxidative Decarboxylation of 2-Aryl Carboxylic Acids Using (Diacetoxyiodo)benzene for Preparation of Aryl Aldehydes, Ketones, and Nitriles

Telvekar¹,

Sasane²

2010

Synlett

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A novel synthetic application of the hypervalent iodine reagent, (diacetoxyiodo)benzene, and catalytic amount of sodium azide in acetonitrile for oxidative decarboxylation of 2-aryl carboxylic acids into corresponding aldehydes, ketones, and nitriles at room temperature is described. The advantages of this protocol are shorter reaction times and mild reaction conditions to obtain moderate to good yields

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Oxidative decarboxylation of .alpha.-hydroxycarboxylic acids with N-iodosuccinimide

Cited by 20 publications

References 2 publications

An Isoquinoline Scaffold as a Novel Class of Allosteric HIV-1 Integrase Inhibitors

An Isoquinoline Scaffold as a Novel Class of Allosteric HIV-1 Integrase Inhibitors

Total Synthesis of Berkelic Acid

Oxidative Decarboxylation of 2-Aryl Carboxylic Acids Using (Diacetoxyiodo)benzene for Preparation of Aryl Aldehydes, Ketones, and Nitriles

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