Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 35, Pages 5799-5802Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201601195
Keywords
Quinolones; Natural products; Antibacterial agents; Cross-coupling; Michael addition
Categories
Funding
- European Reserach Council (ERC) under the European Union [279337/DOS]
- Engineering and Physical Sciences Research Council (EPSRC)
- Biotechnology and BiologicalSciences Research Council (BBSRC)
- Medical Research Council (MRC)
- Cancer Research UK
- Wellcome Trust
- BBSRC
- MRC
- Trinity College Cambridge
- European Research Council (ERC) [279337] Funding Source: European Research Council (ERC)
- Engineering and Physical Sciences Research Council [EP/J016012/1, EP/K039520/1] Funding Source: researchfish
- EPSRC [EP/J016012/1, EP/K039520/1] Funding Source: UKRI
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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.
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