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(-)-Lytophilippine A: Synthesis of a C1-C18 Building Block

  作者 GILLE ANNIKA; HIERSEMANN MARTIN  
  选自 期刊  Organic Letters;  卷期  2010年12-22;  页码  5258-5261  
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[摘要]The convergent enantioselective synthesis of a protected C1-C18 building block for the total synthesis of (-)-lytophilippine A was achieved. A catalytic asymmetric Gosteli-Claisen rearrangement and an Evans aldol reaction served as key C/C-connecting transformations during the assembling of the C1-C7 subunit (10 steps from 4, 29%). The synthesis of the C8-C18 segment was achieved utilizing D-galactose as inexpensive ex-chiral-pool starting material (15 steps, 15%). The merger of the subunits was accomplished by a remarkably efficient sequence consisting of esterification and ring-closing metathesis (five steps, 56%).

 
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