Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 3, Pages 798-801Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b12778
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Funding
- National Institutes of Health [GM-073855, GM-099920]
- Vertex Pharmaceuticals
- AstraZeneca
- Deutsche Forschungsgemeinschaft
- [R24GM111625]
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Metal-catalyzed, double Claisen rearrangement of a bis-allyloxyflavone has been utilized to enable a concise synthesis of the hydrobenzofuro[3,2-b]chromenone core structure of the natural products sanggenon A and sanggenol F. In addition, catalytic, enantioselective [4+2] cycloadditions of 2'-hydroxychalcones have been accomplished using B(OPh)(3)/BINOL complexes. Asymmetric syntheses of the flavonoid Diels-Alder natural products sanggenons C and O have been achieved employing a stereodivergent reaction of a racemic mixture (stereodivergent RRM) involving [4+2] cycloaddition.
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