Evolution of a Strategy for the Enantioselective Synthesis of (−)-Cajanusine

Evolution of a Strategy for the Enantioselective Synthesis of (−)-Cajanusine

The first enantio­selective synthesis of (−)-cajanusine is presented. Key features of the route include a rapid synthesis of the [4.2.0]­bicyclo­octane core by an enantio­selective isomerization/stereo­selective [2+2]-cycloaddition strategy as well as prominent use of catalytic methods for bond cons...

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Veröffentlicht in:Journal of the American Chemical Society 2020-03, Vol.142 (11), p.5002-5006
Hauptverfasser: Guo, Renyu, Witherspoon, Brittany P, Brown, M. Kevin
Format: Artikel
Sprache:eng
Schlagworte:
Bridged Bicyclo Compounds
Catalysis
Cycloaddition Reaction
Metals, Heavy - chemistry
Oxidation-Reduction
Stereoisomerism
Stilbenes - chemical synthesis
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Witherspoon, Brittany P
Brown, M. Kevin
description The first enantio­selective synthesis of (−)-cajanusine is presented. Key features of the route include a rapid synthesis of the [4.2.0]­bicyclo­octane core by an enantio­selective isomerization/stereo­selective [2+2]-cycloaddition strategy as well as prominent use of catalytic methods for bond construction. The evolution of the approach is also presented that highlights unexpected roadblocks and how novel solutions were developed.
doi_str_mv 10.1021/jacs.0c00359
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source MEDLINE; American Chemical Society Journals
subjects Bridged Bicyclo Compounds
Catalysis
Cycloaddition Reaction
Metals, Heavy - chemistry
Oxidation-Reduction
Stereoisomerism
Stilbenes - chemical synthesis
title Evolution of a Strategy for the Enantioselective Synthesis of (−)-Cajanusine
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