From building block to natural products: a short synthesis and complete NMR spectroscopic characterization of (+/-)-anatabine and (+/-)-anabasine

A short and straightforward synthesis of the racemic tobacco alkaloids anatabine and anabasine in five and six steps, respectively, from 3-pyridinecarboxaldehyde utilizing Barbier-type Zn-mediated allylation and ring-closing olefin metathesis, as the key steps, is reported. Additionally, a complete NMR spectroscopic analysis of the final products is carried out and full assignment of the NMR spectra of anatabine and anabasine with accurate coupling constants is accomplished and reported here for the first time. (C) 2011 Elsevier Ltd. All rights reserved.