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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.

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Presentation on theme: "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."— Presentation transcript:

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),

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4 BPS = tert-butyldiphenylsilyl

5 Horner-Wadsworth-Emmons Olefination
Mechanism

6 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.

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24 SEMCl = trimethysilylethoxymethyl chloride

25 Brook Rearrangement

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