potassium carbonate in acetone T=20°C; 20 h;

1: ethyl (5S)-5-hydroxy-3-oxo-7-phenylheptanoate With potassium carbonate in methanol T=20°C; 2 h; 2: dimethyl sulfate in acetone T=20°C;

1.1: 80 percent / sodium borohydride / methanol / 0 - 20 °C 2.1: 46 percent / lipase PS-C / diisopropyl ether / 18 h 3.1: 90 percent / potassium carbonate / methanol 4.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 4.2: tetrahydrofuran / -78 °C 5.1: TFA / CH2Cl2 / 10 h 6.1: potassium carbonate / acetone View Scheme

titanium(IV) isopropylate; (R)-2,2'-dihydroxy-1,1'-binaphthyl; 4-(chloromethyl)-pyridine hydrochloride in toluene T=28°C; Diels-Alder reaction; optical yield given as percent eeenantioselective reaction;

(S,S)-1-naphthyl-TADDOL in toluene T=-60°C; 48 h; Title compound not separated from byproducts;

1.1: nBuLi / hexane; tetrahydrofuran / 0.33 h / 0 °C 1.2: 80 percent / hexane; tetrahydrofuran / 2 h / 20 °C 2.1: 98 percent / H2 / Pd/C / methanol / 8 h / 20 °C 3.1: 97 percent / aq. HCl / methanol / 1 h / 20 °C 4.1: 75 percent / pyridine / 12 h / -17 °C 5.1: 89 percent / ethanol; H2O / 12 h / 20 °C 6.1: Zn / tetrahydrofuran / 0.17 h / 50 °C / ultrasonic irradiation 6.2: 69 percent / tetrahydrofuran / 5.5 h / 50 °C / ultrasonic irradiation 7.1: 84 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 20 °C 8.1: 86 percent / K2CO3 / acetone / 20 h / 20 °C View Scheme

1.1: 98 percent / H2 / Pd/C / methanol / 8 h / 20 °C 2.1: 97 percent / aq. HCl / methanol / 1 h / 20 °C 3.1: 75 percent / pyridine / 12 h / -17 °C 4.1: 89 percent / ethanol; H2O / 12 h / 20 °C 5.1: Zn / tetrahydrofuran / 0.17 h / 50 °C / ultrasonic irradiation 5.2: 69 percent / tetrahydrofuran / 5.5 h / 50 °C / ultrasonic irradiation 6.1: 84 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 20 °C 7.1: 86 percent / K2CO3 / acetone / 20 h / 20 °C View Scheme

1.1: 46 percent / lipase PS-C / diisopropyl ether / 18 h 2.1: 90 percent / potassium carbonate / methanol 3.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 3.2: tetrahydrofuran / -78 °C 4.1: TFA / CH2Cl2 / 10 h 5.1: potassium carbonate / acetone View Scheme

1.1: 85 percent / NaH; n-BuLi / tetrahydrofuran / 0 °C 2.1: 80 percent / sodium borohydride / methanol / 0 - 20 °C 3.1: 46 percent / lipase PS-C / diisopropyl ether / 18 h 4.1: 90 percent / potassium carbonate / methanol 5.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 5.2: tetrahydrofuran / -78 °C 6.1: TFA / CH2Cl2 / 10 h 7.1: potassium carbonate / acetone View Scheme

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 78 percent / tetrahydrofuran; hexane / 1.17 h / -78 - 20 °C 2.1: (S,S)-1-naphthyl-TADDOL / toluene / 48 h / -60 °C View Scheme