Aluminum Chloride-Mediated Dieckmann Cyclization for the Synthesis of Cyclic 2‑Alkyl-1,3-alkanediones: One-Step Synthesis of the Chiloglottones

Cyclic 2-alkyl-1,3-alkanediones
are ubiquitous structural motifs
in many natural products of biological importance. Reported herein
is an AlCl3·MeNO2-mediated Dieckmann cyclization
reaction of general synthetic utility that enables direct access to
complex 2-alkyl-1,3-dione building blocks from readily available dicarboxylic
acid and acid chloride substrates. This new strategy enables direct
synthetic access to the chiloglottone plant pheromones from commercial
material in a single synthetic transformation.