Regiocontrolled dieckmann condensation of 3,4-Bis(methoxycarbonylmethyl) levoglucosenone derivative

Iskakova, M. M.; Biktagirov, I. M.; Файзуллина, Л. Х.; Салихов, Ш. М.; Safarov, M. G.; Валеев, Ф. А.

doi:10.1134/s1070428014010205

Cited by 8 publications

(6 citation statements)

References 6 publications

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“…[18,19] Not only is ad ifferent functionality introduced relatively easily,b ut the removalo ft he reactivek etone group is alsoa dvantageous. [18,19] Not only is ad ifferent functionality introduced relatively easily,b ut the removalo ft he reactivek etone group is alsoa dvantageous.…”

Section: Resultsmentioning

confidence: 99%

“…Inspection of the selected literature compounds suggested that the functional group interconversion of ak etone into the corresponding ketal could be useful to develop solvents from levoglucosenone. [18,19] Not only is ad ifferent functionality introduced relatively easily,b ut the removalo ft he reactivek etone group is alsoa dvantageous. Therefore, ketal derivatives were also considered as solvent candidates, primarily through the reactionofe thylene glycol with the ketone functionality of levoglucosenone.…”

Section: Resultsmentioning

confidence: 99%

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Intelligent Approach to Solvent Substitution: The Identification of a New Class of Levoglucosenone Derivatives

et al. 2016

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With the increasing restriction and control of hazardous solvents, safer alternatives need to be identified. Here a contemporary approach to solvent selection and substitution is presented that offers a more scientific alternative to the simple "like-for-like" exchange. A new family of levoglucosenonederived compounds is proposed, modeled to determine their solvent properties, synthesized, and tested. These new molecules show promise as replacements for polar aprotic solvents that have chronic toxicity issues, such as dichloromethane, nitrobenzene, and N-methylpyrrolidinone. The success of this approach makes it possible for academia and industry to make calculated, intelligent choices for solvent substitution in the future.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Intelligent Approach to Solvent Substitution: The Identification of a New Class of Levoglucosenone Derivatives

et al. 2016

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“…In view of the importance of these substances as flavors and the need for stereoselective routes to 4,5‐disubstituted tetrahydrofuran‐2‐ones their structures have become popular for testing new synthetic methodology . In order to obtain this type of structures, authors applied Diels–Alder reaction with levoglucosenone ( 129 , 130 , 131 , 132 ),, annulation of α‐bromoisolevoglucosenone ( 133 ), Dieckmann condensation over levoglucosenone derivative ( 134 , 135 ) and functionalization of adducts of levoglucosenone by Baeyer–Villiger oxidations ( 136 – 140 ) (Figure ).…”

Section: Enantiospecific Synthesismentioning

confidence: 99%

Levoglucosenone and Its New Applications: Valorization of Cellulose Residues

et al. 2017

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The need to find sustainable alternatives to reduce the dependence on fossil sources has led to significant research efforts on the conversion of biomass into platform chemicals. Modern organic chemistry requires easily obtainable chiral building blocks that show high chemical versatility for their application in the synthesis of enantiopure compounds. The selective pyrolytic conversion of cellulose or cellulose‐containing materials produces levoglucosenone, a highly functionalized chiral structure. This compound has been innovatively used as a template for the synthesis of key intermediates of biologically active products and for the preparation of chiral auxiliaries, catalysts, and organocatalysts for their application in asymmetric synthesis.

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“…As an alternative approach [1] to the synthesis of iridoid skeleton, we have studied transformations of Diels-Alder adduct 1 derived from levoglucosenone and cyclopentadiene [2]. The ability of the endo-R-hydroxy derivative of adduct 1 to undergo intramolecular cyclization to 1,4-epoxide on treatment with m-chloroperoxybenzoic acid (m-CPBA) or I 2 -EtOH [2] allows differentiation of substituents on the double bond.…”

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confidence: 99%

“…1 (1S,2S,3S,4S,5R,6R,7R,8R,9R)-8-Benzyloxy-4,5epoxy-10,12-dioxatetracyclo[7.2.1.1 3,6 .0 2,7 ]tridecane (4) and (1S,2S,3R,4R,6S,7S,8S,10R,11R)-9,12,14-tri-oxapentacyclo[9.2.1.0 2,6 .0 3,10 .0 4,8 ]tetradecan-7-ol (5). m-Chloroperoxybenzoic acid, 2.76 g (16.0 mmol), was added to a solution of 1.18 g (4.0 mmol) of epimeric benzyl ethers 3a/3b in 20.0 mL of chloroform, and the mixture was stirred at room temperature until the initial compounds disappeared (TLC).…”

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confidence: 99%

Intramolecular cationic cyclization of acetoxy derivatives of the levoglucosenone-cyclopentadiene endo-adduct

et al. 2015

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Epoxidation of diastereoisomeric benzyloxy derivatives of the levoglucosenone adduct with cyclopentadiene by treatment with m-chloroperoxybenzoic acid afforded a mixture of 1,2-and 1,4-epoxy derivatives. Intramolecular cyclization of the hydroxy derivatives of the same adduct by the action of I 2 -NaHCO 3 -MeCN gave products resulting from cleavage of the 1,6-anhydro bridge, reduction of the acetal moiety, and olefinaldehyde cyclization. 580 cyclo[6.4.0.0 2,6 .0 3,10 .0 5,9 ]dodec-11-yl}methanol (10). A solution of 1.0 g (5.20 mmol) of 2a/2b in 35.0 mL of acetonitrile was cooled to 0°C, 0.87 g (10.40 mmol) of NaHCO 3 and 2.65 g (10.40 mmol) of I 2 were added, and the mixture was stirred for 1 h at room temperature (TLC). The mixture was treated with 10 mL of water and extracted with ethyl acetate (3 × 40 mL), The extract was washed with an aqueous solution of Na 2 S 2 O 3 and with water and dried over MgSO 4 ; the solvent was distilled off, and the residue was subjected to silica gel chromatography to isolate 0.34 g (26%) of iodide 8, 0.11 g (11%) of hydroxy ketone 9, and 0.13 g (15%) of compound 10.Compound 9. Oily material, R f 0.35 (petroleum ether-EtOAc, 1 : 1), [α] D 20 = -162.9° (c = 1.4, CHCl 3 ). 1 H NMR spectrum (C 6 D 6 ), δ, ppm: 0.82 d and 1.21 d (1H each, 11-H, 2 J = 8.4 Hz), 2.26 d.d.d (1H, 2-H, 3 J 2, 7 = 3.1, 3 J 2, 3 = 3 J 2, 1 = 10.6 Hz), 2.33 d.d (1H, 7-H, 3 J 7, 2 = 3.1, 3 J 7, 8 = 10.4 Hz), 2.36 m (1H, 1-H), 2.61 d.d.d.d (1H, 3-H, 3 J 3, 1′A = 2.8, 3 J 3, 1′B = 6.8, 3 J 3, 2 = 10.6 Hz), 3.21 m (1H, 8-H), 3.38 d.d (1H, 5-H A , 3 J 5A, 7 = 1.0, 2 J = 18.0 Hz), 3.46 d.d (1H, 1′-H A , 3 J 1′A, 3 = 2.8, 2 J = 11.8 Hz), 3.77 d.d (1H, 1′-H B , 3 J 1′B, 3 = 6.8, 2 J = 11.8 Hz), 3.95 d (1H, 5-H B , 2 J = 18.0 Hz), 5.61 d.d

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Regiocontrolled dieckmann condensation of 3,4-Bis(methoxycarbonylmethyl) levoglucosenone derivative

Cited by 8 publications

References 6 publications

Intelligent Approach to Solvent Substitution: The Identification of a New Class of Levoglucosenone Derivatives

Intelligent Approach to Solvent Substitution: The Identification of a New Class of Levoglucosenone Derivatives

Levoglucosenone and Its New Applications: Valorization of Cellulose Residues

Intramolecular cationic cyclization of acetoxy derivatives of the levoglucosenone-cyclopentadiene endo-adduct

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