Lewis acid-triggered selective zincation of chromones, quinolones, and thiochromones: application to the preparation of natural flavones and isoflavones

Lydia Klier; Tomke Bresser; Tobias A Nigst; Konstantin Karaghiosoff; Paul Knochel

doi:10.1021/ja306178q

Lewis acid-triggered selective zincation of chromones, quinolones, and thiochromones: application to the preparation of natural flavones and isoflavones

J Am Chem Soc. 2012 Aug 22;134(33):13584-7. doi: 10.1021/ja306178q. Epub 2012 Aug 9.

Authors

Lydia Klier¹, Tomke Bresser, Tobias A Nigst, Konstantin Karaghiosoff, Paul Knochel

Affiliation

¹ Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 Munich, Germany.

PMID: 22860983
DOI: 10.1021/ja306178q

Abstract

A Lewis acid-triggered zincation allows the regioselective metalation of various chromones and quinolones. In the absence of MgCl(2), a C(3) zincation is observed, whereas in the presence of MgCl(2) or a related Lewis acid, C(2) zincation occurs. Applications to a natural flavone, isoflavone, and quinolone are shown.

Publication types

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

MeSH terms

Biological Products / chemical synthesis
Chromones / chemical synthesis
Chromones / chemistry*
Flavones / chemical synthesis*
Isoflavones / chemical synthesis*
Lewis Acids / chemistry*
Quinolones / chemical synthesis
Quinolones / chemistry*
Stereoisomerism
Zinc / chemistry*

Substances

Biological Products
Chromones
Flavones
Isoflavones
Lewis Acids
Quinolones
Zinc