1: Garner's aldehyde With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane T=20°C; Inert atmosphere; 2: pentadec-1-yne With n-butyllithium in tetrahydrofuran T=-78°C; 0.25 h; Inert atmosphere; 3: in tetrahydrofuran T=-78 - 20°C; 0.25 h; Inert atmosphereEnzymatic reaction;

Swern oxidation;

oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine in dichloromethane T=-78 - -45°C; Swern oxidation;

1: 76 percent / nBuLi / tetrahydrofuran 2: 81 percent / oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - -45 °C View Scheme

1: 76 percent / nBuLi / tetrahydrofuran 2: 81 percent / oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - -45 °C View Scheme

1: 93 percent 2: 70 percent / H(1+) 3: 85 percent / DIBAL / toluene / -78 °C 4: tetrahydrofuran / -78 - 0 °C 5: 80 percent / Swern oxidation View Scheme

1: 95 percent / Et3N / dioxane; H2O 2: 93 percent 3: 70 percent / H(1+) 4: 85 percent / DIBAL / toluene / -78 °C 5: tetrahydrofuran / -78 - 0 °C 6: 80 percent / Swern oxidation View Scheme

1: 70 percent / H(1+) 2: 85 percent / DIBAL / toluene / -78 °C 3: tetrahydrofuran / -78 - 0 °C 4: 80 percent / Swern oxidation View Scheme

1: 85 percent / DIBAL / toluene / -78 °C 2: tetrahydrofuran / -78 - 0 °C 3: 80 percent / Swern oxidation View Scheme

1: L-Selectride 2: 85 percent / p-TsOH / methanol 3: 95 percent / HCl / ethyl acetate 4: 70 percent / LiAlH4 / 1,2-dimethoxy-ethane / 12 h / Heating View Scheme