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We present a short and efficient way of synthesizing two synthetically versatile 4-quinolone-3-carboxylate building blocks by cyclopropanation-ring expansion of 3-chloroindoles with α-halodiazoacetates as the key step. This novel transformation was applied towards the synthesis of the antibiotic drug norfloxacin.
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http://dx.doi.org/10.3762/bjoc.15.212 | DOI Listing |
Beilstein J Org Chem
September 2019
Department of Chemistry, University of Oslo, P.O. Box 1033 Blindern, NO-0315 Oslo, Norway.
We present a short and efficient way of synthesizing two synthetically versatile 4-quinolone-3-carboxylate building blocks by cyclopropanation-ring expansion of 3-chloroindoles with α-halodiazoacetates as the key step. This novel transformation was applied towards the synthesis of the antibiotic drug norfloxacin.
View Article and Find Full Text PDFBeilstein J Org Chem
December 2015
Department of Chemistry, University of Oslo, P.O. Box 1033 Blindern, NO-0315 Oslo, Norway.
In this letter, we report a novel synthesis of ethyl quinoline-3-carboxylates from reactions between a series of indoles and halodiazoacetates. The formation of the quinoline structure is probably the result of a cyclopropanation at the 2- and 3-positions of the indole followed by ring-opening of the cyclopropane and elimination of H-X.
View Article and Find Full Text PDFOrg Biomol Chem
February 2011
School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand.
The ring system of the fungal metabolite (-)-TAN-2483B has been synthesised, for the first time, from d-mannose, utilising a cyclopropanation/ring expansion sequence.
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