Development of a bio-inspired acyl-anion equivalent macrocyclization and synthesis of a trans-resorcylide precursor |
| |
Authors: | Mennen Steven M Miller Scott J |
| |
Affiliation: | Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3860, USA. |
| |
Abstract: | 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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|