Issue 48, 2010
From the journal:

Chemical Communications

Asymmetric total synthesis of (+)-fumimycinvia1,2-addition to ketimines†

Patrick J. Gross,a   Filipp Furche,b   Martin Niegerc  and  Stefan Bräse*a  

* Corresponding authors

a Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, D-76131 Karlsruhe, Germany
E-mail: braese@kit.edu
Fax: +49 721-608-8581

b University of California, Irvine, Department of Chemistry, 1102 Natural Sciences II, Irvine, USA
E-mail: filipp.furche@uci.edu
Fax: +1 949 824-8571

c Laboratory of Inorganic Chemistry, University of Helsinki, 00014 University of Helsinki, Finland

Abstract

The first asymmetric total synthesis of fumimycin was accomplished. As a key step, a 1,2-addition of methyl Grignard reagents to ketimines with quinine as additive was employed. The absolute configuration of (+)-fumimycin was determined by CD-spectroscopy combined with time-dependent density functional calculations.

Graphical abstract: Asymmetric total synthesis of (+)-fumimycin via 1,2-addition to ketimines

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Article information

DOI
https://doi.org/10.1039/C0CC03399E
Article type
Communication
Submitted
22 Aug 2010
Accepted
05 Oct 2010
First published
28 Oct 2010

Chem. Commun., 2010,46, 9215-9217

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Asymmetric total synthesis of (+)-fumimycin via 1,2-addition to ketimines

P. J. Gross, F. Furche, M. Nieger and S. Bräse, Chem. Commun., 2010, 46, 9215 DOI: 10.1039/C0CC03399E

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