1: 73 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature 2: diisobutyl aluminum hydride 3: 2.) aq. acetic acid View Scheme

1: 98 percent / deacylation 2: 73 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature 3: diisobutyl aluminum hydride 4: 2.) aq. acetic acid View Scheme

1: 84 percent / TBAF 2: 98 percent / deacylation 3: 73 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature 4: diisobutyl aluminum hydride 5: 2.) aq. acetic acid View Scheme

1: NaBH4 2: protected as tetrahydropyranyl ether 3: 84 percent / TBAF 4: 98 percent / deacylation 5: 73 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature 6: diisobutyl aluminum hydride 7: 2.) aq. acetic acid View Scheme

1: 72 percent / Pd(MeCN)2Cl2 / tetrahydrofuran / 4 h / Ambient temperature 2: NaBH4 3: 74 percent / acetylation 4: TBAF 5: DIBAL 6: 53 percent View Scheme

1: Pd(MeCN)2Cl2 / tetrahydrofuran / 2 h / Ambient temperature 2: NaBH4 3: protected as tetrahydropyranyl ether 4: 84 percent / TBAF 5: 98 percent / deacylation 6: 73 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature 7: diisobutyl aluminum hydride 8: 2.) aq. acetic acid View Scheme

1: protected as tetrahydropyranyl ether 2: 84 percent / TBAF 3: 98 percent / deacylation 4: 73 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature 5: diisobutyl aluminum hydride 6: 2.) aq. acetic acid View Scheme

tin(ll) chloride

1.1: CuCN / tetrahydrofuran; diethyl ether / 1 h / -30 °C 1.2: tetrahydrofuran; diethyl ether / 8 h / -12 °C 2.1: pyridinium p-toluenesulfonate / CHCl3 / 12 h / 20 °C 3.1: O3 / CH2Cl2 / -78 °C 3.2: Ph3P / CH2Cl2 / 12 h / 20 °C 4.1: benzene / 7 h / 65 °C 5.1: DIBAL-H / toluene; hexane / 1 h / -78 °C 6.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 0 °C 7.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 7.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C 8.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 9.1: Dess-Martin reagent / CH2Cl2 / 1 h / 0 °C 10.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C 11.1: imidazole / dimethylformamide / 7 h / 20 °C 12.1: O3; O2 / CH2Cl2 / -78 °C 12.2: PPh3 / CH2Cl2 / 12 h / 20 °C 13.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 13.2: tetrahydrofuran / 0.25 h 14.1: methanol; diethyl ether / 0 °C 15.1: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 16.1: DMAP; pyridine / CH2Cl2 / 2 h / 20 °C 17.1: Dowex50W / methanol / 0.5 h / 50 °C 18.1: Et3N; DMAP / CH2Cl2 / 36 h / 20 °C 19.1: pyridinium p-toluenesulfonate / CH2Cl2 / 12 h / 20 °C 20.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C 21.1: PCC; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C 22.1: NaH / tetrahydrofuran / 0.08 h / 20 °C 22.2: tetrahydrofuran / 1 h 23.1: LiAlH4; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C 24.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C 25.1: 1.0 M aq. NaOH / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: pyridinium p-toluenesulfonate / CHCl3 / 12 h / 20 °C 2.1: O3 / CH2Cl2 / -78 °C 2.2: Ph3P / CH2Cl2 / 12 h / 20 °C 3.1: benzene / 7 h / 65 °C 4.1: DIBAL-H / toluene; hexane / 1 h / -78 °C 5.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 0 °C 6.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 6.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C 7.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 8.1: Dess-Martin reagent / CH2Cl2 / 1 h / 0 °C 9.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C 10.1: imidazole / dimethylformamide / 7 h / 20 °C 11.1: O3; O2 / CH2Cl2 / -78 °C 11.2: PPh3 / CH2Cl2 / 12 h / 20 °C 12.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 12.2: tetrahydrofuran / 0.25 h 13.1: methanol; diethyl ether / 0 °C 14.1: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 15.1: DMAP; pyridine / CH2Cl2 / 2 h / 20 °C 16.1: Dowex50W / methanol / 0.5 h / 50 °C 17.1: Et3N; DMAP / CH2Cl2 / 36 h / 20 °C 18.1: pyridinium p-toluenesulfonate / CH2Cl2 / 12 h / 20 °C 19.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C 20.1: PCC; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C 21.1: NaH / tetrahydrofuran / 0.08 h / 20 °C 21.2: tetrahydrofuran / 1 h 22.1: LiAlH4; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C 23.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C 24.1: 1.0 M aq. NaOH / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme