155193-07-0Relevant articles and documents
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.
Radical cyclization of α-bromo aluminum acetals onto alkenes and alkynes (radic[al] process): A simple access to γ-lactols and 4-methylene-γ-lactols
Boussonniere, Anne,Beneteau, Romain,Zimmermann, Nicolas,Lebreton, Jacques,Denes, Fabrice
, p. 5613 - 5627 (2011/06/22)
An efficient preparation of γ-lactols and methylene-γ-lactols is described. Highly acid-sensitive lactols are prepared in a concise manner by using a radical cyclization of aluminum acetals. The precursors for the radical reactions are readily prepared fr
Formation of Angularly-Fused Triquinanes by Successive Use of the Pauson-Khand Reaction and Radical Closure
Clive, Derrick L. J.,Cole, Derek C.,Tao, Yong
, p. 1396 - 1406 (2007/10/02)
Angularly-fused triquinanes (see Table 1) are accessible by sequential use of the Pauson-Khand reaction and radical cyclization.The Pauson-Khand step works in the presence of homolyzable bonds, such as C-Br and C-SePh.The method seems best suited to the p
