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Keywords = Dieckman condensation

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12 pages, 1211 KiB  
Article
Regioselective De Novo Synthesis of Phenolic Isoprenoids Grifolin and Neogrifolin
by Boram Lim, Huisu Yeo, Seunghyo Han, Dabin Kim, Hansuk Lee and Sangho Koo
Appl. Sci. 2025, 15(3), 1438; https://doi.org/10.3390/app15031438 - 30 Jan 2025
Viewed by 889
Abstract
The total synthesis of biologically and pharmacologically important phenolic isoprenoids, grifolin and neogrifolin, was developed through simple allylation and cyclization procedures using only ethyl acetoacetate, ethyl crotonate, and farnesyl bromide as substrates. The regioisomeric terpenophenols, which consist solely of orcinol and farnesyl moieties, [...] Read more.
The total synthesis of biologically and pharmacologically important phenolic isoprenoids, grifolin and neogrifolin, was developed through simple allylation and cyclization procedures using only ethyl acetoacetate, ethyl crotonate, and farnesyl bromide as substrates. The regioisomeric terpenophenols, which consist solely of orcinol and farnesyl moieties, cannot be synthesized purely by direct coupling between the units. The regioselectivity issue was solved by controlling the timing of the allylation of β-ketoester with farnesyl bromide and the cyclization with ethyl crotonate. 2-Farnesyl-5-methyl-cyclohexane-1,3-dione and 6-farnesyl-5-methyl-cyclohexane-1,3-dione were prepared in a highly regioselective manner from ethyl acetoacetate in overall yields of 43% and 40%, respectively. The oxidative aromatization of the regioisomeric cyclohexane-1,3-diones produced grifolin and neogrifolin, respectively. Full article
(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)
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13 pages, 1702 KiB  
Article
Synthesis of Thieno[3,2-b]thiophenes from 2,5-Dicarbonyl 3-Nitrothiophenes via Nucleophilic Aromatic Substitution of the Nitro Group with Thiolates
by Roman A. Irgashev and Nikita A. Kazin
Organics 2024, 5(4), 507-519; https://doi.org/10.3390/org5040027 - 7 Nov 2024
Viewed by 1984
Abstract
In this study, we developed an efficient strategy for constructing thieno[3,2-b]thiophene molecules from 3-nitrothiophenes, containing carbonyl fragments at the C-2 and C-5 atoms, by nucleophilic aromatic substitution of the nitro group in these substrates. It was shown that the reaction of [...] Read more.
In this study, we developed an efficient strategy for constructing thieno[3,2-b]thiophene molecules from 3-nitrothiophenes, containing carbonyl fragments at the C-2 and C-5 atoms, by nucleophilic aromatic substitution of the nitro group in these substrates. It was shown that the reaction of 3-nitrothiophene-2,5-dicarboxylates with thiophenols, thioglycolates and 2-mercaptoacetone in the presence of K2CO3 proceeds rapidly via nucleophilic displacement of the nitro group with the formation of 3-sulfenylthiophene-2,5-dicarboxylates. Further treatment of the resulting thiophene-2,5-dicarboxylates, which have -SCH2CO2Alk or -SCH2COMe moiety at C-3 atom, with sodium alcoholates afford obtaining 2,3,5-trisubstituted thieno[3,2-b]thiophene derivatives according to the Dieckman condensation. In turn, the reaction of methyl 5-formyl-4-nitrothiophene-2-carboxylate with methyl thioglycolate or 2-mercaptoacetone in the presence of K2CO3 proceeds to directly form 2,5-disubstituted thieno[3,2-b]thiophenes. Full article
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