Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 16, Pages 5744-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja9014716
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Funding
- NSF [CHE-0619638]
- Columbia University, Amgen
- ACS PRF [47481-G]
- Camille and Henry Dreyfus Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [844593] Funding Source: National Science Foundation
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The napyradiomycins are an intriguing family of halogenated natural products with activity against several tumor cell lines as well as some of the worst bacterial strains known to humanity, including methicillin-resistant Staphylococcus aureas and vancomycin-resistant strains of Enterococcus faecium. This communication delineates the first asymmetric total synthesis of (-)-napyradiomycin A1 by a strategy that features a two-step total synthesis of flaviolin, the first highly asymmetric halogenation of a simple alkene, and a Johnson-Claisen rearrangement that: generates a quaternary carbon next to a glucal-like oxygen.
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