216227-75-7Relevant academic research and scientific papers
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.
experimental part, 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
Total synthesis of rubrolide M and some of its unnatural congeners
Bellina, Fabio,Anselmi, Chiara,Rossi, Renzo
, p. 2023 - 2027 (2007/10/03)
Two protocols have been developed for the Pd-catalyzed regioselective synthesis of 4-aryl-3-chloro-2(5H)-furanones starting from 3,4-dichloro-2(5H)-furanone. These monochloro derivatives have then been used as precursors to (Z)-4-aryl-5-[1-(aryl)methylidene]-3-chloro-2(5H)-furanones including naturally-occurring rubrolide M.
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.
