Abstract:
Action of bases on levoglucosenone-derived 6-oxononan-9-olide and 7-oxodecan-10-olide causes the transannular reaction of the aldol type affording stable 2-acylcyclopent-1-en-1-ol and 2-acylcyclohex-1-en-1-ol, respectively. The lower homologue, 5-oxooctan-8-olide derivative, under the similar conditions gives a complex mixture of products, which may be explained by the poor stability of the intermediate 2-acyl-cyclobut-1-en-1-ol.
Document Type:
Article
Language: English
Citation:
L. Kh. Faizullina, Yu. S. Galimova, Yu. A. Khalilova, Sh. M. Salikhov, F. A. Valeev, “Aldol-type transformations of levoglucosenone-derived medium-sized keto lactones”, Mendeleev Commun., 28:5 (2018), 482–484
Linking options:
https://www.mathnet.ru/eng/mendc1807
https://www.mathnet.ru/eng/mendc/v28/i5/p482
This publication is cited in the following 4 articles:
Caio M. Pacheco, Wesley Lima, Fernanda A. Lima, Mauro R. B. P. Gomez, Isabela G. da Silva, Leandro S. M. Miranda, Pierre M. Esteves, Ivaldo Itabaiana, Robert Wojcieszak, Raquel A. C. Leão, Rodrigo O. M. A. de Souza, “Levoglucosenone as a starting material for cascade continuous-flow synthesis of (R)-γ-carboxy-γ-butyrolactone”, RSC Adv., 14:47 (2024), 34611
Liliya Kh. Faizullina, Yulia S. Galimova, Shamil M. Salikhov, Farid A. Valeev, “Michael Adducts of Levoglucosenone with α-Ethoxycarbonyl- and α-Nitrocyclododecanones: Transformation into Chiral Macrolides”, Chem Heterocycl Comp, 56:11 (2020), 1434
Liliya Kh. Faizullina, Yuliya A. Khalilova, Shamil M. Salikhov, Farid A. Valeev, “Reverse ketal-acetal rearrangement of levoglucosenone and cyclohexanone Michael adducts and the possibilities of its use in the synthesis of native topology lactones”, Chem Heterocycl Comp, 55:7 (2019), 612
L. Kh. Faizullina, Yu. S. Galimova, M. Yu. Ovchinnikov, Sh. M. Salikhov, S. L. Khursan, F. A. Valeev, “Reversible intramolecular Dieckmann-type condensation of 2-(2-hydroxymethyl-5,5,6-trimethoxytetrahydropyran-3-ylcarbonyl)-cyclopentanone: an alternative access to medium-sized lactones”, Mendeleev Commun., 29:1 (2019), 64–66
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