- Asymmetric Synthesis of Homocitric Acid Lactone
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A short, diastereoselective synthesis of homocitric acid lactone is described. The key step is a bioinspired aldol addition to set the stereogenic center in an intermediate that requires only modest oxidation state manipulation to complete the synthesis. This approach enables rapid generation of isotopomers in which carbon and hydrogen can be replaced by heavier nuclei at nearly every position.
- Nickerson, Leslie A.,Huynh, Valerie,Balmond, Edward I.,Cramer, Stephen P.,Shaw, Jared T.
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p. 11404 - 11408
(2016/11/28)
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- Enantioselective synthesis of isotopically labeled homocitric acid lactone
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A concise synthesis of homocitric acid lactone was developed to accommodate systematic placement of carbon isotopes (specifically 13C) for detailed studies of this cofactor. This new route uses a chiral allylic alcohol, available in multigram quantities from enzymatic resolution, as a starting material, which transposes asymmetry through an Ireland-Claisen rearrangement.
- Moore, Jared T.,Hanhan, Nadine V.,Mahoney, Maximillian E.,Cramer, Stephen P.,Shaw, Jared T.
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p. 5615 - 5617
(2013/12/04)
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- An improved synthesis of trisodium (U)-homocitrate from citric acid
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A method of synthesis of trisodium (R)-homocitrate starting from citric acid is reported. The procedure affords the final product of high optical purity with satisfactory yield.
- Prokop,Milewska
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experimental part
p. 1317 - 1322
(2010/07/05)
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- Enantioselective synthesis of (R)-homocitric acid lactone
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An expedient enantioselective approach to (R)-homocitric acid lactone from an ephedrine-derived morpholine-dione, a cationic glycolate equivalent, is described.
- Pansare, Sunil V.,Adsool, Vikrant A.
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p. 7099 - 7101
(2008/03/11)
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- A facile method for synthesis of (R)-(-)- and (S)-(+)-homocitric acid lactones and related α-hydroxy dicarboxylic acids from D- or L-malic acid
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We report here a simple and convenient route for the stereoselective synthesis of (R)-(-)- and (S)-(+)-homocitric acid lactones, which play very important roles in biochemistry. The method involves only three steps, starting from the readily available met
- Xu, Peng-Fei,Matsumoto, Tsuyoshi,Ohki, Yasuhiro,Tatsumi, Kazuyuki
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p. 3815 - 3818
(2007/10/03)
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- A short enantioselective synthesis of homocitric acid-γ-lactone and 4-hydroxy-homocitric acid-γ-lactones
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A simple method for the synthesis of enantiopure homocitric acid γ-lactone and its 4-hydroxy analogues starting from spiro-γ- dilactone, in up to 74% isolated yield is described.
- Paju, Anne,Kanger, T?nis,Pehk, T?nis,Eek, Margus,Lopp, Margus
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p. 9081 - 9084
(2007/10/03)
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- Resolution of a citric acid derivative: Synthesis of (R)-(-)-homocitric acid-γ-lactone
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Both the (R) and (S) enantiomers of the citric acid derivative 1 have been obtained in ≤90% ee via resolution of the racemate by fractional crystallisation of the (S) and (R)-α-methylbenzylamine salts respectively. The stereochemistry of (R)-1 has been assigned by its conversion to (R)-(-)- homocitric acid utilising an Amdt-Eistert homologation followed by acid eatalysed deprotection.
- Ancliff, Rachael A.,Russell, Andrew T.,Sanderson, Adam J.
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p. 3379 - 3382
(2007/10/03)
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- Enantioselective syntheses of (-)- and (+)-homocitric acid lactones
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Highly enantioselective syntheses of enantiomers of homocitric acid lactones (R)-5a and (S)-5b are described. Thermal Diels-Alder cycloadditions of 2a and 2b to 1,3-butadiene produced adducts 3a and 3b, respectively. Oxidative ozonolysis of latter adducts gave products 4a and 4b which after acid treatment afforded a mixture with 5a and 5b as major component. Acid lactones 5a and 5b were converted into their dimethyl esters 6a and 6b which were purified by chromatography. After saponification, the products obtained were crystallized to yield (-)- and (+)-homocitric acid lactones ((R)-5a and (S)-5b). Diastereomeric excess (de) of Diels-Alder adducts 3a and 3b was determined by means of Mosher esters of glycols 8a, 8b, and racemic 8. Diels-Alder cycloaddition products of lactones 2a and 2b to 1,3-butadiene showed a diastereoselectivity of 96%.
- Rodriguez R., Gaston H.,Biellmann, Jean-Francois
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p. 1822 - 1824
(2007/10/03)
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