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Divergent Synthesis of Quinolone Natural Products from Pseudonocardia sp. CL38489.

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.

SUBMITTER: Geddis SM

PROVIDER: S-EPMC5215369 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Divergent Synthesis of Quinolone Natural Products from Pseudonocardia sp. CL38489.

Geddis Stephen M SM Carro Laura L Hodgkinson James T JT Spring David R DR

European journal of organic chemistry 20161115 35

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 modula ...[more]

PMID: 28111524

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