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Divergent Synthesis of Quinolone Natural Products from Pseudonocardia sp. CL38489
Author(s) -
Geddis Stephen M.,
Carro Laura,
Hodgkinson James T.,
Spring David R.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601195
Subject(s) - chemistry , quinolone , amination , regioselectivity , allylic rearrangement , combinatorial chemistry , stereochemistry , intramolecular force , natural product , allylic alcohol , organic chemistry , catalysis , antibiotics , biochemistry
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.