Asymmetric synthesis of 4′-C-benzyl-2′,3′-dideoxynucleoside analogues from 3-benzyl-2-hydroxy-2-cyclopenten-1-one

Jõgi, Artur; Ilves, Marit; Paju, Anne; Pehk, Tõnis; Kailas, Tiiu; Müürisepp, Aleksander-Mati; Lopp, Margus

doi:10.1016/j.tetasy.2008.01.028

Cited by 18 publications

(7 citation statements)

References 18 publications

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“…The synthesis of cyclopentane-1,2-dione derivative 28 ( 50 ) ( Scheme 9 ) was accomplished in two steps by reacting known dipotassium salt 45 ( 51 ) with benzyl bromide to give intermediate 46 , followed by a debenzylation/decarboxylation sequence of the latter to obtain the desired 1,2-dione. The 1,2-dione 29 ( 52 ) was synthesized via magnesium methoxide induced cyclization of α,β-unsaturated dione 47 .…”

Section: Experimental Sectionmentioning

confidence: 99%

Structure Property Relationships of Carboxylic Acid Isosteres

et al. 2016

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The replacement of a carboxylic acid with a surrogate structure, or (bio)-isostere, is a classical strategy in medicinal chemistry. The general underlying principle is that by maintaining the features of the carboxylic acid critical for biological activity, but appropriately modifying the physicochemical properties, improved analogs may result. In this context, a systematic assessment of the physicochemical properties of carboxylic acid isosteres would be desirable to enable more informed decisions of potential replacements to be used for analog design. Herein we report the structure-property relationships (SPR) of 35 phenylpropionic acid derivatives, in which the carboxylic acid moiety is replaced with a series of known isosteres. The dataset generated provides an assessment of the relative impact on the physicochemical properties that these replacements may have compared to the carboxylic acid analog. As such, this study presents a framework for how to rationally apply isosteric replacements of the carboxylic acid functional group.

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Section: Experimental Sectionmentioning

confidence: 99%

Structure Property Relationships of Carboxylic Acid Isosteres

et al. 2016

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“…The absolute configuration of the obtained iodolactone was determined to be R by comparison of the specific rotation after conversion to known 5‐benzyl‐5‐(hydroxymethyl)dihydrofuran‐2(3 H )‐one ((i) KOH, THF–H 2 O; (ii) 1 M aq. HCl) …”

Section: Enantioselective Iodocyclizationmentioning

confidence: 99%

Stereoselective Electrophilic Cyclization

Sakakura

Ishihara

2015

The Chemical Record

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Electrophilic cyclizations of unactivated alkenes play highly important roles in the synthesis of useful building blocks. This account describes our contributions to the rational design of monofunctionalized chiral Lewis base catalysts for enantioselective iodo‐ and protocyclizations. For the stereoselective promotion of electrophilic bromocyclizations, nucleophilic phosphite–urea cooperative catalysts have been designed.

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“…The compound 10 is a key intermediate for the synthesis of nucleoside analogues, therapeutic agents against AIDS and cancer. [25] The three-step transformation of 10 gave the corresponding ester 11 in 91 % yield.…”

Section: Angewandte Chemiementioning

confidence: 99%

Cooperative Activation with Chiral Nucleophilic Catalysts and N‐Haloimides: Enantioselective Iodolactonization of 4‐Arylmethyl‐4‐pentenoic Acids

et al. 2014

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Chiral triaryl phosphates promote the enantioselective iodolactonization of 4-substituted 4-pentenoic acids to give the corresponding iodolactones in high yields with high enantioselectivity. N-Chlorophthalimide (NCP) is employed as a Lewis acidic activator and oxidant of I2 for the present iodolactonization. In combination with 1.5 equivalents of NCP, only 0.5 equivalents of I2 are sufficient to generate the iodinating reagent.

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Asymmetric synthesis of 4′-C-benzyl-2′,3′-dideoxynucleoside analogues from 3-benzyl-2-hydroxy-2-cyclopenten-1-one

Cited by 18 publications

References 18 publications

Structure Property Relationships of Carboxylic Acid Isosteres

Structure Property Relationships of Carboxylic Acid Isosteres

Stereoselective Electrophilic Cyclization

Cooperative Activation with Chiral Nucleophilic Catalysts and N‐Haloimides: Enantioselective Iodolactonization of 4‐Arylmethyl‐4‐pentenoic Acids

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