C.A. Morales Olefin Addition Rxns in Polyether Synthesis-3 Chem 206 Application of the model for syn-oxidative Application of the model for syn-oxidative polycyclization using an all(2)-polyolefin polycyclization on an all (E)-polyolefin OH (E,E, Er-pregoniocin triene (ZZZ)premonensin triene Et2Zn, Ti(o-+Pr)4 ADmxβ OH Et C12H25 CrO3(py)2 Me 1)AC20, EtaN cat. DMAP HO A Et o 2)NaBH4, CeCl3 n-C12H25(Cl2CHCO)20 Me (Cl2CHCO2)Reo (Cl2CHCO)20 One stereocenter(★ controls the induction n-c,Hos of six additional centers Ho C D n-C12H25 Meo niacin HO2C Monensin McDonald, F. E. Pure App. Chem., 1998, 70, 35Me Me Et Me O Me Me Me HO H Et O Me O Me Me Et Me O Me HO2C Me OH Me OH H O LnM O Me Et Me Me HO OH O Me Me Me AcO H Et OH (Cl2CHCO2)ReO3 (Cl2CHCO)2O O Me Me AcO H Et O Me H H OH C D O O O O O Me MeO Me HO2C HO Me Me Me Me H Et H H H OH Me OH H C D HO O O Me O Et H H O H H O H H OH n-C12H25 n-C12H25 O H n-C12H25 OH Et O H H O H H O H H OH n-C12H25 HO O O Me n-C12H25 OH (Cl2CHCO2)ReO3 (Cl2CHCO)2O NHSO2CF3 NHSO2CF3 Application of the model for syn-oxidative polycyclization using an all (Z)-polyolefin: McDonald, F. E. Pure App. Chem., 1998, 70, 355. (Z,Z,Z)-premonensin triene Monensin C. A. Morales Olefin Addition Rxns in Polyether Synthesis-3 Chem 206 AD-mix b CrO3(py)2 1) Ac2O, Et3N cat. DMAP 2) NaBH4, CeCl3 5 Goniocin 5 (E,E,E)-pregoniocin triene Et2Zn, Ti(O-i-Pr)4 * * One stereocenter ( ) controls the induction of six additional centers. * Application of the model for syn-oxidative polycyclization on an all (E)-polyolefin: