37828-78-7Relevant academic research and scientific papers
Microwave-Assisted Organocatalyzed Rearrangement of Propargyl Vinyl Ethers to Salicylaldehyde Derivatives: An Experimental and Theoretical Study
Tejedor, David,Cotos, Leandro,Márquez-Arce, Daniel,Odriozola-Gimeno, Mikel,Torrent-Sucarrat, Miquel,Cossío, Fernando P.,García-Tellado, Fernando
supporting information, p. 18280 - 18289 (2015/12/24)
The microwave-assisted imidazole-catalyzed transformation of propargyl vinyl ethers (PVEs) into multisubstituted salicylaldehydes is described. The reaction is instrumentally simple, scalable, and tolerates a diverse degree of substitution at the propargylic position of the starting PVE. The generated salicylaldehyde motifs incorporate a broad range of topologies, spanning from simple aromatic monocycles to complex fused polycyclic systems. The reaction is highly regioselective and takes place under symmetry-breaking conditions. The preparative power of this reaction was demonstrated in the first total synthesis of morintrifolin B, a benzophenone metabolite isolated from the small tree Morinda citrifolia L. A DFT study of the reaction was performed with full agreement between calculated values and experimental results. The theoretically calculated values support a domino mechanism comprising a propargyl Claisen rearrangement, a [1,3]-H shift, a [1,7]-H shift (enolization), a 6π electrocyclization, and an aromatization reaction.
Total synthesis of parvaquone and the serendipitous discovery of a novel chromium-mediated method for β-lactone formation
Harrity, Joseph P. A.,Kerr, William J.,Middlemiss, David,Scott, James S.
, p. 219 - 227 (2007/10/03)
During attempts to synthesise the 2-hydroxy-1,4-naphthoquinone, parvaquone, 1, a novel chromium-mediated method for the synthesis of functionalised β-lactones from propargyl alcohols has been discovered. Additionally, using both dry state and ultrasound conditions, the total synthesis of parvaquone (1) has been achieved; the most efficient techniques deliver this target compound in up to 46% overall yield over, as low as, two synthetic processes.
