Chiron Approach for the Total Synthesis of Brevipolide M

Abstract

An efficient stereoselective synthesis of brevipolide M was established in 13 linear steps and 17.8% overall yields base on chiron approach. The key steps of our synthesis involved tandem homologation / tetrahydrofuran cyclization and sequential ring-closing metathesis (RCM) / double-bond migration in one-pot processes.

Steglich esterification: A versatile synthetic approach toward the synthesis of natural products, their analogues/derivatives

“…Brevipolide M belongs to pyrone-based natural compounds which have been found to exhibit numerous biological activities. In 2022, Liu et al aimed at total synthesis of Brevipolide M by employing ring-closing metathesis, Wittig olefination and Steglich esterification in 17.8 % overall yield in 13 linear steps [ 50 ]. The synthesis was actualized from d -mannofuranose diacetonide 94 which was transformed to compound 95 over a few steps.…”