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A Protecting Group Free Synthesis of (?-Neostenine via the [5 + 2] Photocycloaddition of Maleimides.

  作者 Lainchbury, Michael D.;Medley, Marcus I.;Taylor, Piers M.;Hirst, Paul;Dohle, Wolfgang;Booker-Milburn, Kevin I.;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2008年73-17;  页码  6497-6505  
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[摘要]A concise, linear synthesis of the Stemona alkaloid (?-neostenine (I) is reported. Key features include an organocopper-mediated bislactone C2-desymmetrization for the stereoselective construction of the cyclohexane-lactone C,D-rings. The assembly of the fused pyrrolo[1,2-a]azepine core was achieved by application of a [5 + 2] maleimide photocycloaddn. A custom FEP flow reactor was used to successfully overcome the scale limitations imposed by a classical immersion well batch reactor. The synthesis was completed in 14 steps from furan, in 9.5% overall yield, without the use of any protecting groups.

 
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