Abstract:
Starting from levoglucosenone piperilene Diels–Alder adduct a total synthesis of sarcodictyin A analogue containing 14-methyl group and C(12)=C(13) bond in ring A was performed, where the key step was the intramolecular cyclization between acetylene and aldehyde moieties to produce a 10-membered carbocycle.
Citation:
B. T. Sharipov, A. A. Pershin, F. A. Valeev, “Synthesis of sarcodictyin A analogue containing 14-methyl group and C(12)=C(13) bond in ring A from levoglucosenone”, Mendeleev Commun., 27:2 (2017), 119–121
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https://www.mathnet.ru/eng/mendc1915
https://www.mathnet.ru/eng/mendc/v27/i2/p119
This publication is cited in the following 11 articles:
L. Kh. Faizullina, Yu. S. Galimova, A. S Ryabova, N. F Galimzyanova, F. A Valeev, “Synthesis of 4-isopropyl derivatives of levoglucosenone”, Žurnal organičeskoj himii, 59:6 (2023), 797
Amandine L. Flourat, Lorenzo Pezzana, Sabrina Belgacem, Abdouramane Dosso, Marco Sangermano, Sami Fadlallah, Florent Allais, “Levoglucosenone to 3D-printed green materials: synthesizing sustainable and tunable monomers for eco-friendly photo-curing”, Green Chem., 25:19 (2023), 7571
L. Kh. Faizullina, A. R. Tagirov, Sh. M. Salikhov, F. A. Valeev, “Ene reaction of Diels–Alder adducts of levoglucosenone and 1,3-dienes with acetaldehyde”, Mendeleev Commun., 33:1 (2023), 9–10
L. Kh. Faizullina, Yu. S. Galimova, A. S. Ryabova, N. F. Galimzianova, F. A. Valeev, “Synthesis of 4-Isopropyl Derivatives of Levoglucosenone”, Russ J Org Chem, 58:12 (2022), 1797
Bulat T. Sharipov, Anna N. Davydova, Farid A. Valeev, “Synthesis of S(3)–S(8) eleutheside blocks from levoglucosenone”, Chem Heterocycl Comp, 56:8 (2020), 982
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
B. T. Sharipov, A. N. Davydova, L. Kh. Faizullina, F. A. Valeev, “Preparation of the diastereomerically pure 2S-hydroxy derivative of dihydrolevoglucosenone (cyrene)”, Mendeleev Commun., 29:2 (2019), 200–202
Bulat T. Sharipov, Anna N. Davidova, Farid A. Valeev, “Aromatization of 2,2,5-trialkyl-substituted 2,5-dihydrofurans and factors affecting their stabilization”, Chem Heterocycl Comp, 54:4 (2018), 403
María B. Comba, Yi‐hsuan Tsai, Ariel M. Sarotti, María I. Mangione, Alejandra G. Suárez, Rolando A. Spanevello, “Levoglucosenone and Its New Applications: Valorization of Cellulose Residues”, Eur J Org Chem, 2018:5 (2018), 590
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
T. V. Ghochikyan, M. A. Samvelyan, A. S. Galstyan, V. M. Muzalevskiy, V. G. Nenajdenko, “Copper catalyzed alkyne–azide cycloaddition with 3-propargyl- γ-butyrolactones”, Mendeleev Commun., 27:6 (2017), 562–564
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