1.1: 95 percent / DDQ / CH2Cl2; H2O / 1.5 h / 25 °C 2.1: 93 percent / i-Pr2NEt; DMAP / CH2Cl2 / 0.5 h / 25 °C 3.1: 84 percent / Bu3SnH; (Ph3P)4Pd / benzene / 2.5 h / 25 °C 4.1: 83 percent / iPr2NEt; 1-methyl-2-pyrrolidinone; (CH3CN)2PdCl2 / 2 h / 25 °C 5.1: 98 percent / DIBAL-H / toluene / 0.08 h / -78 °C 6.1: 97 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 25 °C 7.1: BuLi / toluene; hexane / 0.25 h / -78 °C 7.2: toluene; hexane / 0.25 h / -78 °C 8.1: 140 mg / NaHCO3; Dess-Martin periodinane / CH2Cl2 / 1 h / 25 °C 9.1: 75 percent / t-BuOK / toluene; tetrahydrofuran / 2 h / 0 °C 10.1: CeCl3; t-BuLi / tetrahydrofuran; diethyl ether / 0.17 h / -78 °C 10.2: tetrahydrofuran; diethyl ether; toluene / 0.08 h / -78 °C 11.1: PPTS / 2 h / 25 °C 12.1: Et3N / DMAP / CH2Cl2 / 1 h 13.1: 2,6-lutidine / CH2Cl2 / 0.75 h / -20 °C 14.1: aq. HCl / acetone / 2 h / -15 - 0 °C 15.1: 40 percent / Ag2CO3-Celite / benzene / 2 h / 80 °C 16.1: PCl3; pyridine / 0.25 h / 25 °C 16.2: 1 h 17.1: 3.9 mg / aq. H2O2 / CH2Cl2; pyridine / 0.5 h 18.1: aq. HF / acetonitrile / 0.25 h / 25 °C 18.2: aq. HF; pyridine / acetonitrile / 168000 h View Scheme

1: With hydrogen fluoride in acetonitrile T=25°C; 0.25 h; 2: With pyridine; hydrogen fluoride in acetonitrile 168000 h; Further stages.;

1.1: BuLi / toluene; hexane / 0.25 h / -78 °C 1.2: toluene; hexane / 0.25 h / -78 °C 2.1: 140 mg / NaHCO3; Dess-Martin periodinane / CH2Cl2 / 1 h / 25 °C 3.1: 75 percent / t-BuOK / toluene; tetrahydrofuran / 2 h / 0 °C 4.1: CeCl3; t-BuLi / tetrahydrofuran; diethyl ether / 0.17 h / -78 °C 4.2: tetrahydrofuran; diethyl ether; toluene / 0.08 h / -78 °C 5.1: PPTS / 2 h / 25 °C 6.1: Et3N / DMAP / CH2Cl2 / 1 h 7.1: 2,6-lutidine / CH2Cl2 / 0.75 h / -20 °C 8.1: aq. HCl / acetone / 2 h / -15 - 0 °C 9.1: 40 percent / Ag2CO3-Celite / benzene / 2 h / 80 °C 10.1: PCl3; pyridine / 0.25 h / 25 °C 10.2: 1 h 11.1: 3.9 mg / aq. H2O2 / CH2Cl2; pyridine / 0.5 h 12.1: aq. HF / acetonitrile / 0.25 h / 25 °C 12.2: aq. HF; pyridine / acetonitrile / 168000 h View Scheme

1.1: 97 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 25 °C 2.1: BuLi / toluene; hexane / 0.25 h / -78 °C 2.2: toluene; hexane / 0.25 h / -78 °C 3.1: 140 mg / NaHCO3; Dess-Martin periodinane / CH2Cl2 / 1 h / 25 °C 4.1: 75 percent / t-BuOK / toluene; tetrahydrofuran / 2 h / 0 °C 5.1: CeCl3; t-BuLi / tetrahydrofuran; diethyl ether / 0.17 h / -78 °C 5.2: tetrahydrofuran; diethyl ether; toluene / 0.08 h / -78 °C 6.1: PPTS / 2 h / 25 °C 7.1: Et3N / DMAP / CH2Cl2 / 1 h 8.1: 2,6-lutidine / CH2Cl2 / 0.75 h / -20 °C 9.1: aq. HCl / acetone / 2 h / -15 - 0 °C 10.1: 40 percent / Ag2CO3-Celite / benzene / 2 h / 80 °C 11.1: PCl3; pyridine / 0.25 h / 25 °C 11.2: 1 h 12.1: 3.9 mg / aq. H2O2 / CH2Cl2; pyridine / 0.5 h 13.1: aq. HF / acetonitrile / 0.25 h / 25 °C 13.2: aq. HF; pyridine / acetonitrile / 168000 h View Scheme

1.1: 98 percent / DIBAL-H / toluene / 0.08 h / -78 °C 2.1: 97 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 25 °C 3.1: BuLi / toluene; hexane / 0.25 h / -78 °C 3.2: toluene; hexane / 0.25 h / -78 °C 4.1: 140 mg / NaHCO3; Dess-Martin periodinane / CH2Cl2 / 1 h / 25 °C 5.1: 75 percent / t-BuOK / toluene; tetrahydrofuran / 2 h / 0 °C 6.1: CeCl3; t-BuLi / tetrahydrofuran; diethyl ether / 0.17 h / -78 °C 6.2: tetrahydrofuran; diethyl ether; toluene / 0.08 h / -78 °C 7.1: PPTS / 2 h / 25 °C 8.1: Et3N / DMAP / CH2Cl2 / 1 h 9.1: 2,6-lutidine / CH2Cl2 / 0.75 h / -20 °C 10.1: aq. HCl / acetone / 2 h / -15 - 0 °C 11.1: 40 percent / Ag2CO3-Celite / benzene / 2 h / 80 °C 12.1: PCl3; pyridine / 0.25 h / 25 °C 12.2: 1 h 13.1: 3.9 mg / aq. H2O2 / CH2Cl2; pyridine / 0.5 h 14.1: aq. HF / acetonitrile / 0.25 h / 25 °C 14.2: aq. HF; pyridine / acetonitrile / 168000 h View Scheme

1.1: CeCl3; t-BuLi / tetrahydrofuran; diethyl ether / 0.17 h / -78 °C 1.2: tetrahydrofuran; diethyl ether; toluene / 0.08 h / -78 °C 2.1: PPTS / 2 h / 25 °C 3.1: Et3N / DMAP / CH2Cl2 / 1 h 4.1: 2,6-lutidine / CH2Cl2 / 0.75 h / -20 °C 5.1: aq. HCl / acetone / 2 h / -15 - 0 °C 6.1: 40 percent / Ag2CO3-Celite / benzene / 2 h / 80 °C 7.1: PCl3; pyridine / 0.25 h / 25 °C 7.2: 1 h 8.1: 3.9 mg / aq. H2O2 / CH2Cl2; pyridine / 0.5 h 9.1: aq. HF / acetonitrile / 0.25 h / 25 °C 9.2: aq. HF; pyridine / acetonitrile / 168000 h View Scheme

1.1: 75 percent / t-BuOK / toluene; tetrahydrofuran / 2 h / 0 °C 2.1: CeCl3; t-BuLi / tetrahydrofuran; diethyl ether / 0.17 h / -78 °C 2.2: tetrahydrofuran; diethyl ether; toluene / 0.08 h / -78 °C 3.1: PPTS / 2 h / 25 °C 4.1: Et3N / DMAP / CH2Cl2 / 1 h 5.1: 2,6-lutidine / CH2Cl2 / 0.75 h / -20 °C 6.1: aq. HCl / acetone / 2 h / -15 - 0 °C 7.1: 40 percent / Ag2CO3-Celite / benzene / 2 h / 80 °C 8.1: PCl3; pyridine / 0.25 h / 25 °C 8.2: 1 h 9.1: 3.9 mg / aq. H2O2 / CH2Cl2; pyridine / 0.5 h 10.1: aq. HF / acetonitrile / 0.25 h / 25 °C 10.2: aq. HF; pyridine / acetonitrile / 168000 h View Scheme

1: 88 percent / Pd(MeCN)2Cl2 / dimethylformamide / 0 °C 2: tetrazole / CH2Cl2 / 0 °C 3: t-BuOOH / CH2Cl2 / 0 °C 4: HCO2NH2; PPh3 / Pd(PPh3)4 / tetrahydrofuran 5: 79 percent / aq. HF; pyridine / acetonitrile View Scheme

1: tetrazole / CH2Cl2 / 0 °C 2: t-BuOOH / CH2Cl2 / 0 °C 3: HCO2NH2; PPh3 / Pd(PPh3)4 / tetrahydrofuran 4: 79 percent / aq. HF; pyridine / acetonitrile View Scheme

1: 91 percent / 2,6-lutidine / CH2Cl2 / -78 °C 2: 99 percent / DDQ; H2O / CH2Cl2 / 0 °C 3: 100 percent / Dess-Martin periodinane / CH2Cl2 / 0 °C 4: 98 percent / CeCl3 / tetrahydrofuran / -50 °C 5: 95 percent / Dess-Martin periodinane / CH2Cl2 / 0 °C 6: 63 percent / NaI; AcOH / 20 °C 7: 81 percent / aq. HF; pyridine / acetonitrile / 0 °C 8: 99 percent / Me4NB(OAc)3H / acetic acid; acetonitrile / -30 °C 9: 88 percent / 2,6-lutidine / CH2Cl2 / -78 °C 10: 88 percent / Pd(MeCN)2Cl2 / dimethylformamide / 0 °C 11: tetrazole / CH2Cl2 / 0 °C 12: t-BuOOH / CH2Cl2 / 0 °C 13: HCO2NH2; PPh3 / Pd(PPh3)4 / tetrahydrofuran 14: 79 percent / aq. HF; pyridine / acetonitrile View Scheme