946084-16-8Relevant articles and documents
Development of a bio-inspired acyl-anion equivalent macrocyclization and synthesis of a trans-resorcylide precursor
Mennen, Steven M.,Miller, Scott J.
, p. 5260 - 5269 (2008/02/07)
(Chemical Equation Presented) Studies on the macrocyclization of α,ω-dialdehydes have revealed a strong dependence on ring size with respect to the ultimate efficiency of the reaction. Strong catalyst dependence was observed, as thiazolium salts led to no detectable product formation, whereas electron-deficient triazolium salts served as precatalysts for the cyclization. Surprisingly, the N-pentafluorophenyl triazolium variant led to cyclization at room temperature within a short 90-min reaction time. These findings were applied to a range of substrates, including the synthesis of a key intermediate in a rapid synthesis of trans-resorcylide.
