1.1: EDCI; DMAP / CH2Cl2 / 0 - 20 °C 2.1: 78 percent / second generation Grubbs' catalyst / toluene / 110 °C 3.1: KHMDS / tetrahydrofuran; toluene / 0 °C 3.2: 76 percent / tetrahydrofuran; toluene / -78 - -20 °C 4.1: 97 percent / HF*pyridine / tetrahydrofuran / 3 h / 20 °C 5.1: 91 percent / TrisNHNH2; Et3N / 1,2-dichloro-ethane / 7 h / 50 °C View Scheme

1.1: 84 percent / LiAlH4 / diethyl ether / 3 h / -78 °C 2.1: 85 percent / Ph3P; CBr4 / CCl4 / 3 h / 20 °C 3.1: 86 percent / 3 h / 160 °C 4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 5.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 5.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 6.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 7.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 7.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 8.1: pyridine / CH2Cl2 / 1 h / 0 °C 9.1: CH2Cl2 / 5 h / 20 °C 10.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 11.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 12.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 13.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 14.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 2.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 2.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 3.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 4.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 5.1: pyridine / CH2Cl2 / 1 h / 0 °C 6.1: CH2Cl2 / 5 h / 20 °C 7.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 8.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 9.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 10.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 11.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 1.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 2.1: pyridine / CH2Cl2 / 1 h / 0 °C 3.1: CH2Cl2 / 5 h / 20 °C 4.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 5.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 6.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 7.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 8.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

1.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 2.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 3.1: pyridine / CH2Cl2 / 1 h / 0 °C 4.1: CH2Cl2 / 5 h / 20 °C 5.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 6.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 7.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 8.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 9.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

1.1: KHMDS / tetrahydrofuran; toluene / 0 °C 1.2: 76 percent / tetrahydrofuran; toluene / -78 - -20 °C 2.1: 97 percent / HF*pyridine / tetrahydrofuran / 3 h / 20 °C 3.1: 91 percent / TrisNHNH2; Et3N / 1,2-dichloro-ethane / 7 h / 50 °C View Scheme

1.1: 78 percent / second generation Grubbs' catalyst / toluene / 110 °C 2.1: KHMDS / tetrahydrofuran; toluene / 0 °C 2.2: 76 percent / tetrahydrofuran; toluene / -78 - -20 °C 3.1: 97 percent / HF*pyridine / tetrahydrofuran / 3 h / 20 °C 4.1: 91 percent / TrisNHNH2; Et3N / 1,2-dichloro-ethane / 7 h / 50 °C View Scheme

1.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 2.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 3.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 3.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 4.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 5.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating View Scheme

1.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 2.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 2.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 3.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 4.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating View Scheme

1: 0.052 g / NaBH4 / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 2: 94 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 3: 92 percent / HF*pyridine / tetrahydrofuran / 2 h / 0 - 20 °C View Scheme