1.1: 100 percent / polystyrene-NEt2 / CH2Cl2 / 2.75 h / 0 - 20 °C 2.1: pentane / 3.25 h / 0 °C 2.2: 100 percent / MeOH / pentane / 5 h / 0 - 20 °C 3.1: 100 percent / Amberlite IRC-50 / 1.25 h / 20 °C 4.1: LDA / tetrahydrofuran / 2 h / -78 - -15 °C 4.2: 94 percent / tetrahydrofuran / -78 - -40 °C View Scheme

1: 88 percent / Bu2BOTf; DIPEA / CH2Cl2 / 1 h / -78 °C 2: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 3: 76 percent / lithium hydroxide; hydrogen peroxide / tetrahydrofuran; H2O / 4 h / 20 °C 4: 71 percent / borane-dimethyl sulfide; trimethyl borate / tetrahydrofuran / 9 h / 0 - 15 °C 5: 72 percent / imidazole / CH2Cl2 / 3 h / 0 °C View Scheme

1.1: O3 / CH2Cl2 / 0.17 h / -78 °C 1.2: 93 percent / polymer-supported triphenylphosphine / CH2Cl2 / 14 h / 20 °C 2.1: 77 percent / BH3*THF / tetrahydrofuran / 0.25 h / 20 °C 3.1: 100 percent / diethylamino-polystyrene / CH2Cl2 / 2.5 h / 0 °C 4.1: 100 percent / pentane / 3.5 h / 0 °C 5.1: LDA / hexane; tetrahydrofuran / 0.17 h / -78 - -15 °C 5.2: 94 percent / hexane; tetrahydrofuran / 2 h / -78 - -40 °C View Scheme

1: (3S)-3-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-5-oxo-heptanal With sodium tetrahydroborate in ethanol; dichloromethane T=-78°C; 1 h; 2: tert-butyldimethylsilyl chloride With 1H-imidazole in dichloromethane T=20°C; 16 h; Further stages.;

1: 98 percent / morpholinomethyl polystyrene / CH2Cl2 / 20 h / 20 °C 2: 77 percent / DIBAL-H / hexane; tetrahydrofuran / 1 h / -78 °C 3: 100 percent / pyridinium chloroformate/basic alumina / CH2Cl2 / 20 h / 20 °C 4: 98 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C 5: 98 percent / pyridinium chlorochromate/basic alumina / CH2Cl2 / 20 h / 20 °C View Scheme

1.1: 96 percent / polystyrene-DMAP / CH2Cl2 / 2.5 h / 20 °C 2.1: O3 / CH2Cl2 / 0.33 h / -78 °C 2.2: 93 percent / polystyrene-PPh2 / CH2Cl2 / 12 h / -78 - 20 °C 3.1: N-Ts-D-phenylalanine; BH3*THF / CH2Cl2 / 0.25 h / -94 °C 3.2: CH2Cl2 / 1.75 h / -94 - -78 °C 3.3: 93 percent / Amberlite IRA-743 / CH2Cl2; H2O / 6 h / -78 - 20 °C 4.1: 100 percent / polystyrene-NEt2 / CH2Cl2 / 2.75 h / 0 - 20 °C 5.1: pentane / 3.25 h / 0 °C 5.2: 100 percent / MeOH / pentane / 5 h / 0 - 20 °C 6.1: 100 percent / Amberlite IRC-50 / 1.25 h / 20 °C 7.1: LDA / tetrahydrofuran / 2 h / -78 - -15 °C 7.2: 94 percent / tetrahydrofuran / -78 - -40 °C View Scheme

triethylamine

1: 65 percent / 3-hydroxypyridine / Co2(CO)8 / tetrahydrofuran / 24 h / 65 °C / 38786.1 Torr 2: 96.4 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 20 °C 3: 98 percent / NaBH4; CaCl2 / tetrahydrofuran; ethanol / 18 h / 20 °C 4: 85 percent / imidazole / dimethylformamide / 3 h / 20 °C 5: 96.5 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C View Scheme

1: 98 percent / 2,6-lutidine / CH2Cl2 / 0.75 h / -78 °C 2: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 3: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min 4: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h View Scheme

1: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 2: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min 3: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h View Scheme