1: tetrahydrofuran; diethyl ether / 1 h / 0 °C 2: CH2Cl2 / 12 h / 20 °C 4: 50 percent / pyridinium dichromate, pyridinium trifluoroacetate / CH2Cl2 / 10 h / Ambient temperature 5: 1.) LDA / 1.) THF, hexane, -78 deg C, 8 h, 2.) THF, hexane, RT, 12 h 6: 93 percent / Pd(PPh3)2(OAc)2, CuI, diethylamine / dimethylformamide / 2 h / Ambient temperature 7: H2, quinoline / Lindlar's catalyst / 1.) EtOAc, hexane, RT, 1 h, 2.) isooctane, reflux, 2 h 8: tetrabutylammonium fluoride / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: CH2Cl2 / 12 h / 20 °C 3: 50 percent / pyridinium dichromate, pyridinium trifluoroacetate / CH2Cl2 / 10 h / Ambient temperature 4: 1.) LDA / 1.) THF, hexane, -78 deg C, 8 h, 2.) THF, hexane, RT, 12 h 5: 93 percent / Pd(PPh3)2(OAc)2, CuI, diethylamine / dimethylformamide / 2 h / Ambient temperature 6: H2, quinoline / Lindlar's catalyst / 1.) EtOAc, hexane, RT, 1 h, 2.) isooctane, reflux, 2 h 7: tetrabutylammonium fluoride / tetrahydrofuran / 12 h / Ambient temperature View Scheme

2: 50 percent / pyridinium dichromate, pyridinium trifluoroacetate / CH2Cl2 / 10 h / Ambient temperature 3: 1.) LDA / 1.) THF, hexane, -78 deg C, 8 h, 2.) THF, hexane, RT, 12 h 4: 93 percent / Pd(PPh3)2(OAc)2, CuI, diethylamine / dimethylformamide / 2 h / Ambient temperature 5: H2, quinoline / Lindlar's catalyst / 1.) EtOAc, hexane, RT, 1 h, 2.) isooctane, reflux, 2 h 6: tetrabutylammonium fluoride / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: tetrahydrofuran; diethyl ether / 2 h / 0 °C 2: tetrahydrofuran; diethyl ether / 1 h / 0 °C 3: CH2Cl2 / 12 h / 20 °C 5: 50 percent / pyridinium dichromate, pyridinium trifluoroacetate / CH2Cl2 / 10 h / Ambient temperature 6: 1.) LDA / 1.) THF, hexane, -78 deg C, 8 h, 2.) THF, hexane, RT, 12 h 7: 93 percent / Pd(PPh3)2(OAc)2, CuI, diethylamine / dimethylformamide / 2 h / Ambient temperature 8: H2, quinoline / Lindlar's catalyst / 1.) EtOAc, hexane, RT, 1 h, 2.) isooctane, reflux, 2 h 9: tetrabutylammonium fluoride / tetrahydrofuran / 12 h / Ambient temperature View Scheme