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

A1 Originalartikel i en vetenskaplig tidskrift (referentgranskad)


Interna författare/redaktörer


Publikationens författare: Tiina Saloranta, Reko Leino
Förläggare: PERGAMON-ELSEVIER SCIENCE LTD
Publiceringsår: 2011
Tidskrift: Tetrahedron Letters
Tidskriftsakronym: TETRAHEDRON LETT
Volym: 52
Nummer: 36
Artikelns första sida, sidnummer: 4619
Artikelns sista sida, sidnummer: 4621
Antal sidor: 3
ISSN: 0040-4039


Abstrakt

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.


Nyckelord

Barbier-type allylation, Ring-closing metathesis, Ruthenium, Tobacco alkaloid, Zinc

Senast uppdaterad 2020-26-02 vid 06:06