70680-20-5Relevant academic research and scientific papers
High-Yielding Total Synthesis of Sexually Deceptive Chiloglottones and Antimicrobial Dialkylresorcinols through an Organocatalytic Reductive Coupling Reaction
Madhavachary, Rudrakshula,Ramachary, Dhevalapally B.
supporting information, p. 7317 - 7323 (2016/02/20)
Biologically important, less-explored natural products of sexually deceptive chiloglottones, antimicrobial dialkylresorcinols, and their many analogues were synthesized in very good yields in a sequential two-pot manner by using an "organocatalytic reductive coupling reaction" as the key step. Sexually deceptive chiloglottones, antimicrobial dialkylresorcinols, and their many analogues are synthesized in very good yields in a sequential two-pot manner by using an "organocatalytic reductive coupling reaction" as the key step.
Ion pairing effects on the regioselectivity of arylic versus benzylic C-O bond reductive cleavage: synthetic applications
Azzena, Ugo,Dettori, Giovanna,Mascia, Ilaria,Pisano, Luisa,Pittalis, Mario
, p. 11998 - 12006 (2008/03/14)
The regioselectivity of the reductive cleavage of 3,4,5-trimethoxybenzyl methyl ether strongly depends on the alkali metal employed as a reducing agent and solvent effects. Reactions run using Na as a reducing agent led to aromatic C(4)-O bond cleavage, whilst reductions run in the presence of Na/15-crown-5, or using Li as a reducing agent, led to highly regioselective benzylic C-O bond cleavage. This regioselectivity turnaround is discussed in terms of major solvent effects affecting the fragmentation paths of a common reaction intermediate. Synthetic applications of these findings led to the synthesis of biologically active compounds, like 2,5-dialkyl-substituted resorcinols, or 1-(3,4,5-trimethoxyphenyl)-2-arylethanes structurally related to combretastatin.
