ion-exchange resin AG 50W-X4 in methanol 48 h; Ambient temperaturein the dark;

in tetrahydrofuran; ethanol; nitrogen

1: 1) 2,6-di-tert-butylpyridine, 2a) TMSTf, 2b) Et3N, MeOH / 1) CH2Cl2, -78 deg C, 5 min, 2a) -78 deg C, 2 h, 2b) -78 deg C, 5 min then to RT 2: TiCl4 / CH2Cl2 / 12 h / -78 °C 3: 92 percent / DMAP, i-Pr2NEt / CH2Cl2 / 18 h / 0 °C 4: 91 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C 6: 1) LDA / 1) -78 deg C 7: 94 percent / Et3N / (Ph3P)2PdCl2 / 75 °C 8: H2, Lindlar catalyst, quinoline / hexane 9: 2,2,4-trimethyl-pentane / Heating 10: 82 percent / ion-exchange resin AG 50W-X4 / methanol / 48 h / Ambient temperature; in the dark View Scheme

1: 95 percent / pyridine, ozone / methanol; CH2Cl2 / 0.42 h / -78 °C 2: 1) 2,6-di-tert-butylpyridine, 2a) TMSTf, 2b) Et3N, MeOH / 1) CH2Cl2, -78 deg C, 5 min, 2a) -78 deg C, 2 h, 2b) -78 deg C, 5 min then to RT 3: TiCl4 / CH2Cl2 / 12 h / -78 °C 4: 92 percent / DMAP, i-Pr2NEt / CH2Cl2 / 18 h / 0 °C 5: 91 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C 7: 1) LDA / 1) -78 deg C 8: 94 percent / Et3N / (Ph3P)2PdCl2 / 75 °C 9: H2, Lindlar catalyst, quinoline / hexane 10: 2,2,4-trimethyl-pentane / Heating 11: 82 percent / ion-exchange resin AG 50W-X4 / methanol / 48 h / Ambient temperature; in the dark View Scheme

1: 95 percent / DMAP, pyridine / 14 h / refrigerator 2: 95 percent / pyridine, ozone / methanol; CH2Cl2 / 0.42 h / -78 °C 3: 1) 2,6-di-tert-butylpyridine, 2a) TMSTf, 2b) Et3N, MeOH / 1) CH2Cl2, -78 deg C, 5 min, 2a) -78 deg C, 2 h, 2b) -78 deg C, 5 min then to RT 4: TiCl4 / CH2Cl2 / 12 h / -78 °C 5: 92 percent / DMAP, i-Pr2NEt / CH2Cl2 / 18 h / 0 °C 6: 91 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C 8: 1) LDA / 1) -78 deg C 9: 94 percent / Et3N / (Ph3P)2PdCl2 / 75 °C 10: H2, Lindlar catalyst, quinoline / hexane 11: 2,2,4-trimethyl-pentane / Heating 12: 82 percent / ion-exchange resin AG 50W-X4 / methanol / 48 h / Ambient temperature; in the dark View Scheme

1: 1) LDA / 1) -78 deg C 2: 94 percent / Et3N / (Ph3P)2PdCl2 / 75 °C 3: H2, Lindlar catalyst, quinoline / hexane 4: 2,2,4-trimethyl-pentane / Heating 5: 82 percent / ion-exchange resin AG 50W-X4 / methanol / 48 h / Ambient temperature; in the dark View Scheme

2: 1) LDA / 1) -78 deg C 3: 94 percent / Et3N / (Ph3P)2PdCl2 / 75 °C 4: H2, Lindlar catalyst, quinoline / hexane 5: 2,2,4-trimethyl-pentane / Heating 6: 82 percent / ion-exchange resin AG 50W-X4 / methanol / 48 h / Ambient temperature; in the dark View Scheme

1: 94 percent / Et3N / (Ph3P)2PdCl2 / 75 °C 2: H2, Lindlar catalyst, quinoline / hexane 3: 2,2,4-trimethyl-pentane / Heating 4: 82 percent / ion-exchange resin AG 50W-X4 / methanol / 48 h / Ambient temperature; in the dark View Scheme

1: 91 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C 3: 1) LDA / 1) -78 deg C 4: 94 percent / Et3N / (Ph3P)2PdCl2 / 75 °C 5: H2, Lindlar catalyst, quinoline / hexane 6: 2,2,4-trimethyl-pentane / Heating 7: 82 percent / ion-exchange resin AG 50W-X4 / methanol / 48 h / Ambient temperature; in the dark View Scheme

1: TiCl4 / CH2Cl2 / 12 h / -78 °C 2: 92 percent / DMAP, i-Pr2NEt / CH2Cl2 / 18 h / 0 °C 3: 91 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C 5: 1) LDA / 1) -78 deg C 6: 94 percent / Et3N / (Ph3P)2PdCl2 / 75 °C 7: H2, Lindlar catalyst, quinoline / hexane 8: 2,2,4-trimethyl-pentane / Heating 9: 82 percent / ion-exchange resin AG 50W-X4 / methanol / 48 h / Ambient temperature; in the dark View Scheme