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Total Synthesis of Discodermolide (pt. 2)

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  1. 1. 有機合成化学特論 発表資料 2011-11-20 有末 芳 (M1) TOTAL SYNTHESIS OF DISCODERMOLIDE (pt. 2)
  2. 2. Novel aldol-based approach
  3. 3. Lewis acid-induced addition of allylic silane to aldehyde as key-step
  4. 4. Hybrid of Novartis-Smith-Paterson
  5. 5. Discodermolide: very complex chainlike compound (13 stereocenters) Representative example of current methods for control of acyclic chemistry. - Key enantioselective reaction Allylic boronate, allenyl stannanes, oxazolidinone auxiliaries, boron enolate, and allylic silane - Key coupling strategy Suzuki-Miyaura, Negishi, NHK, and Wittig High degree of convergency, robustness, and scaled-up synthesis!!