M.C. White, M.S. Taylor Chem 15 Nu attack on olefins -332 Week of november 25, 2002 Application of an intramolecular Wacker oxidation in the synthesis of garsubellin A Napdcly(40 mol%) t-BuOoH ACOH/H20 ACOH/H2O -HcI reductive Garsubellin a elimination HCIPdll t-BuOOH Pd"CI 阝- hydride Pdc CP心 d la Shibasaki OL 2002(4)859M.C. White, M.S. Taylor Chem 15 Nu attack on Olefins -332- Week of November 25, 2002 Application of an intramolecular Wacker oxidation in the synthesis of Garsubellin A O O O O HO Garsubellin A Shibasaki OL 2002 (4) 859. O O O O O Na2PdCl4 (40 mol%) t-BuOOH O O O OH HO O O O OH HO Cl2PdII O O O O HO PdIICl2 t-BuOOH PdIICl2 O O O O HO O O O O HO PdIICl AcOH / H2O 69% AcOH / H2O Pd0 – HCl – HCl O O O O HO HClPdII H HCl β-hydride elimination reductive elimination of HCl