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

Ahlam M Armaly; Sukanta Bar; Corinna S Schindler

doi:10.1021/acs.orglett.7b01622

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

Org Lett. 2017 Aug 4;19(15):3958-3961. doi: 10.1021/acs.orglett.7b01622. Epub 2017 Jul 19.

Authors

Ahlam M Armaly¹, Sukanta Bar¹, Corinna S Schindler¹

Affiliation

¹ Department of Chemistry, Willard Henry Dow Laboratory, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109, United States.

PMID: 28723218
DOI: 10.1021/acs.orglett.7b01622

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.