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 transcript:

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

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.

SEMCl = trimethysilylethoxymethyl chloride

Brook Rearrangement