Total Synthesis of Berkeleylactone A

The first total synthesis of the potent antibiotic berkeleylactone A is described in 10 steps with an overall yield of 9.5%. A key step of our concise route is a late-stage, highly diastereoselective, sulfa-Michael addition. The 16-membered macrocyclic lactone was formed via ring closing metathesis...

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Bibliographic Details
Published in:	Journal of organic chemistry Vol. 84; no. 11; pp. 7159 - 7165
Main Authors:	Ferko, Branislav, Zeman, Marián, Formica, Michele, Veselý, Sebastián, Doháňošová, Jana, Moncol, Ján, Olejníková, Petra, Berkeš, Dušan, Jakubec, Pavol, Dixon, Darren J, Caletková, Ol’ga
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 07-06-2019
Online Access:	Get full text
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Summary:	The first total synthesis of the potent antibiotic berkeleylactone A is described in 10 steps with an overall yield of 9.5%. A key step of our concise route is a late-stage, highly diastereoselective, sulfa-Michael addition. The 16-membered macrocyclic lactone was formed via ring closing metathesis and subsequent chemoselective reduction. The absolute stereochemical configuration was confirmed by single-crystal X-ray analysis. Synthetic berkeleylactone A was tested against several methicillin-resistant Staphylococcus aureus strains, and its potent antibacterial activity was verified.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904
DOI:	10.1021/acs.joc.9b00850