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Divergent Synthesis of Quinolone Natural Products from $\textit{Pseudonocardia}$ sp. CL38489

Published version
Peer-reviewed

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Authors

Geddis, SM 
Carro Santos, L 
Hodgkinson, JT 
Spring, DR 

Abstract

Two divergent synthetic routes are reported offering access to four quinolone natural products from Pseudonocardia sp. CL38489. Key steps to the natural products involved a regioselective epoxidation, an intramolecular Buchwald–Hartwig amination and a final acid-catalysed 1,3-allylic-alcohol rearrangement to give two of the natural products in one step. This study completes the synthesis of all eight antibacterial quinolone natural products reported in the family. In addition, this modular strategy enables an improved synthesis towards two natural products previously reported.

Description

Keywords

quinolones, natural products, antibacterial agents, cross-coupling, Michael addition

Journal Title

European Journal of Organic Chemistry

Conference Name

Journal ISSN

1434-193X
1099-0690

Volume Title

2016

Publisher

Wiley
Sponsorship
European Research Council (279337)
Royal Society (WM150022)
Engineering and Physical Sciences Research Council (EP/J016012/1)
Engineering and Physical Sciences Research Council (EP/K039520/1)
The research leading to these results has received funding from the European Reserach Council (ERC) under the European Union's Seventh Framework Programme (FP7/2007-2013) and ERC grant agreement number 279337/DOS. Research in the D. R. S. lab is also supported by the Engineering and Physical Sciences Research Council (EPSRC), Biotechnology and BiologicalSciences Research Council (BBSRC), Medical Research Council (MRC), Cancer Research UK and the Wellcome Trust. Work in the M. W lab is supported by the BBSRC and MRC. J. T. H. was supported by Trinity College Cambridge.