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Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach

  作者 HANSON PAUL R; CHEGONDI RAMBABU; JOHN NGUYEN; THOMAS CHRISTOPHER D; WAETZIG JOSHUA D; WHITEHEAD ALAN  
  选自 期刊  Journal of Organic Chemistry;  卷期  2011年76-11;  页码  4358-4370  
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[摘要]The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,S-p)-5 and (R,R,R-p)-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction, and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclization study to the 24-membered macrolactone 1.

 
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