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BPS = tert-butyldiphenylsilyl

Smith Amos B 3rd; Cox Jason M; Furuichi Noriyuki; Kenesky Craig S; Zheng Junying; Atasoylu Onur; Wuest William M Total synthesis of (-)-2-epi-peloruside A. Organic letters (2008), 10(24), 5501-4. BPS = tert-butyldiphenylsilyl. Horner-Wadsworth-Emmons Olefination. Mechanism.

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BPS = tert-butyldiphenylsilyl

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  1. Smith Amos B 3rd; Cox Jason M; Furuichi Noriyuki; Kenesky Craig S; Zheng Junying; Atasoylu Onur; Wuest William M Total synthesis of (-)-2-epi-peloruside A. Organic letters (2008), 10(24), 5501-4.

  2. BPS = tert-butyldiphenylsilyl

  3. Horner-Wadsworth-Emmons Olefination Mechanism

  4. Stereochemical Outcome of HWE reaction Usually favors formation of E-alkene However…. Still and Gennari found that Z-alkenes could be produced if the highly electron withdrawing trifluoroethylphosphonate is used as shown below.

  5. SEMCl = trimethysilylethoxymethyl chloride

  6. Brook Rearrangement

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