- Concise, stereocontrolled and modular syntheses of the anti-influenza rubrolides R and S
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The fungal metabolites rubrolide R and S were synthesized in concise, entirely stereoselective fashion through the combined use of bromine-stereodirected vinylogous aldol condensation (SVAC) and Suzuki cross-coupling. A bioinspired, high-yield conversion
- Moreira, Thaís A.,Lafleur-Lambert, Rapha?l,Barbosa, Luiz C.A.,Boukouvalas, John
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- Synthetic method for rubrolide compounds E, F, R, S and their derivatives
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Rubrolide F (compound 1f), R (compound 1r), and S (compound 1s), which are biological important natural butenolides, 7andPrime;,8andPrime;-didihydro derivatives (compound 1sa) thereof, 3andPrime; -bromorubrolide (compound 1fa), rubrolide E (compound 1e) and di-O-methyl derivatives thereof (compound 1ea) can be industrially obtained and are effectively synthesized with the overall yield of 14-48.5% from low-priced precursors. The rubrolide compounds can be synthesized through a Knoevenagel condensation reaction after a Wittig-Horner reaction and SeO_2-induced tandem allylic hydroxylation/intramolecular cyclization for preparing butenolide rings and a rubrolide cores structure.COPYRIGHT KIPO 2017
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Paragraph 0158; 0166; 0167
(2018/03/28)
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- Protecting-Group-Free Total Syntheses of Rubrolide R and S
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The two marine natural products rubrolide R (1) and S (2) were synthesised in only three linear steps starting from commercially available tetronic acid without using protecting-group chemistry. Key steps in the syntheses were the Pd-catalysed Suzuki–Miya
- Schacht, Mathias,Boehlich, Gordon Jacob,de Vries, Jessica,Bertram, Stephanie,Gabriel, Gülsah,Zimmermann, Phyllis,Heisig, Peter,Schützenmeister, Nina
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supporting information
p. 1745 - 1748
(2017/04/13)
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- Efficient, collective synthesis and nitric oxide inhibitory activity of rubrolides E, F, R, S and their derivatives
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An efficient first synthesis of biologically significant natural butenolides, rubrolides F (1f), R (1r), S (1s) & its 7″,8″-didehydro derivative (1sa), and 3″-bromo rubrolide (1fa) along with the synthesis of rubrolide E (1e) and its di-O-methyl derivative (1ea) is accomplished in a collective fashion from commercially available and inexpensive precursors in overall yields of 14–48.5%. Key features are Wittig-Horner reaction, SeO2-induced tandem allylic hydroxylation/intramolecular cyclization and Knoevenagel condensation. Next, in their inhibitory activity towards nitric oxide (NO) production in lipopolysaccharide-induced RAW 264.7 macrophages as an indicator of anti-inflammatory activity, all compounds displayed good inhibitory activity in a concentration-dependent manner. None of the compound exhibited notable cytotoxicity at the highest concentration (10?μM) and IC50values are found in the range from 8.53 to 17.85?μM.
- Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
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