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Development of a bio-inspired acyl-anion equivalent macrocyclization and synthesis of a trans-resorcylide precursor. | LitMetric

Development of a bio-inspired acyl-anion equivalent macrocyclization and synthesis of a trans-resorcylide precursor.

J Org Chem

Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3860, USA.

Published: July 2007

Studies on the macrocyclization of alpha,omega-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.

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http://dx.doi.org/10.1021/jo070676dDOI Listing

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