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A Highly Stereoselective Total Synthesis of (+)-9-epi-Dictyostatin

  作者 ZANATO CHIARA; PIGNATARO LUCA; AMBROSI ANDREA; HAO ZHONGYAN; GENNARRI CESARE  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2010年-30;  页码  5767-5771  
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[摘要]The total synthesis of (+)-9-epi-dictyostatin (1b), a diastereomer of the antimitotic marine-sponge-derived macro-tide (-)-dictyostatin (1a), was achieved by creating 11 stereogenic centers and 4 stereogenic double bonds with a high level of stereocontrol. The yield for the 29-step longest linear sequence from Roche ester was 1.53%. The final key steps to this unnatural product were the vinylzincate C10-C26 addition to aldehyde C1-C9 (leading surprisingly to a complete stereoselectivity for the 9R-epimer), followed by Yamaguchi macrolactonization and global deprotection.

 
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