136762-97-5Relevant academic research and scientific papers
A facile synthesis of rubrolide E1
Kar, Anirban,Argade, Narshinha P.
, p. 2284 - 2286 (2005)
A simple and efficient synthesis of rubrolide E (1e) has been demonstrated via Meerwein coupling reaction of para-anisyldiazonium chloride with N-phenylmaleimide (2), regioselective reduction of para-anisylmaleic anhydride (4), Knoevenagel condensation of butyrolactone 5 with para-anisaldehyde and demethylation pathway. Georg Thieme Verlag Stuttgart.
An Approach for the Generation of γ-Propenylidene-γ-butenolides and Application to the Total Synthesis of Rubrolides
Roy, Debayan,Tharra, Prabhakararao,Baire, Beeraiah
supporting information, p. 5605 - 5610 (2021/08/01)
Design and synthesis of a new class of γ-butenolides, viz. β-aryl-γ-propenylidene-γ-butenolides, have been reported from β-aryl-Z-enoate propargylic alcohols in the presence of acid. Isolation of β-aryl-γ-propenylidene-γ-butenolides and their O18-isomer c
Efficient, collective synthesis and nitric oxide inhibitory activity of rubrolides E, F, R, S and their derivatives
Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
, p. 50 - 53 (2016/12/23)
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.
Palladium-catalyzed hydrodehalogenation of butenolides: An efficient and sustainable access to β-arylbutenolides
Karak, Milandip,Barbosa, Luiz C.A.,Maltha, Celia R.A.,Silva, Thiago M.,Boukouvalas, John
, p. 2830 - 2834 (2017/06/27)
Several α-unsubstituted β-arylbutenolides have been prepared in 69–92% yield by reductive dehalogenation of α-halo-β-arylbutenolides. The latter were assembled in a single-step from α,β-dihalobutenolides, which are accessible on a large-scale from biomass-derived furfural. Our dehalogenation protocol is illustrated by a new synthesis of the marine antibiotics rubrolide E and F, and 3″-bromorubrolide F.
New concise and efficient synthesis of rubrolides C and e via intramolecular Wittig reaction
Tale, Nilesh P.,Shelke, Amol V.,Tiwari, Girdharilal B.,Thorat, Prerana B.,Karade, Nandkishor N.
, p. 852 - 857 (2012/06/16)
A short total synthesis of rubrolides C and E has been achieved in four steps, using readily available 4-methoxyacetophenone, 2-bromoacetic acid, and the appropriate aromatic aldehyde, in 46 and 45% yield, respectively. Key reactions involved are α-tosyloxylation of the aryl methyl ketone, intramolecular Wittig reaction, Knoevenagel condensation, and demethylation. Copyright
Short and efficient synthesis of rubrolide E
Chavan, Subhash P.,Pathak, Ashok B.,Pandey, Ankur,Kalkote, Uttam R.
, p. 4253 - 4263 (2008/03/13)
Short and efficient synthesis of rubrolide E from commercially available 4-methoxyacetophenone, employing ring-closing metathesis, Knoevenagel condensation, and Reformatsky reactions, are the key steps are described. Copyright Taylor & Francis Group, LLC.
Facile access to 4-aryl-2(5H)-furanones by suzuki cross coupling: Efficient synthesis of rubrolides C and E
Boukouvalas, John,Lachance, Nicolas,Ouellet, Michel,Trudeau, Martin
, p. 7665 - 7668 (2007/10/03)
The Pd(0)-catalyzed cross coupling between 4-bromo-2(5H)-furanones and arylboronic acids provides the corresponding 4-aryl-2(5H)-furanones in yields of 61-85%. By using this method in conjunction with furanolate chemistry, the marine antibiotics rubrolide C and E have been synthesized in highly efficient fashion (4 steps, overall yield = 61 and 56% respectively) from β- tetronic acid.
