Title: | "Aluminum Chloride-Mediated Dieckmann Cyclization for the Synthesis of Cyclic 2-Alkyl-1,3-alkanediones: One-Step Synthesis of the Chiloglottones" |
Author(s): | Armaly AM; Bar S; Schindler CS; |
Address: | "Department of Chemistry, Willard Henry Dow Laboratory, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109, United States" |
DOI: | 10.1021/acs.orglett.7b01622 |
ISSN/ISBN: | 1523-7052 (Electronic) 1523-7052 (Linking) |
Abstract: | "Cyclic 2-alkyl-1,3-alkanediones are ubiquitous structural motifs in many natural products of biological importance. Reported herein is an AlCl(3).MeNO(2)-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" |
Notes: | "PubMed-not-MEDLINEArmaly, Ahlam M Bar, Sukanta Schindler, Corinna S eng Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S. 2017/07/21 Org Lett. 2017 Aug 4; 19(15):3958-3961. doi: 10.1021/acs.orglett.7b01622. Epub 2017 Jul 19" |