1.1: NaH; imidazole / tetrahydrofuran 2.1: various solvent(s) / 1 h / 240 °C 3.1: TsOH; MeOH / CH2Cl2 4.1: Et3N; DMAP / CH2Cl2 5.1: Pd(OAc)2; DPPP; Bu4NOAc / 1 h / 20 °C 5.2: NaBH4 5.3: NaOMe; MeOH 6.1: (COCl)2; DMSO; Et3N 7.1: tetrahydrofuran / -78 - 20 °C 8.1: (COCl)2; DMSO; Et3N / CH2Cl2 9.1: tBuOK / tetrahydrofuran 9.2: 75 percent / tetrahydrofuran / 4 h / -30 - 20 °C 10.1: AcOH; H2O / tetrahydrofuran / 24 h / 20 °C 11.1: NaBH4 / methanol 12.1: CBr4; PPh3 / acetonitrile / 0 °C 12.2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / -40 °C 13.1: tetrahydrofuran / -78 °C 14.1: LiHMDS / tetrahydrofuran / -78 °C 14.2: 80 percent / tetrahydrofuran 15.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 15.2: 85 percent / nBu4NF / tetrahydrofuran 16.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 16.2: 60 percent / DMAP / toluene / 80 °C 17.1: 86 percent / TFA / CH2Cl2 / 0 °C 18.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme

1.1: Et3N; DMAP / CH2Cl2 2.1: Pd(OAc)2; DPPP; Bu4NOAc / 1 h / 20 °C 2.2: NaBH4 2.3: NaOMe; MeOH 3.1: (COCl)2; DMSO; Et3N 4.1: tetrahydrofuran / -78 - 20 °C 5.1: (COCl)2; DMSO; Et3N / CH2Cl2 6.1: tBuOK / tetrahydrofuran 6.2: 75 percent / tetrahydrofuran / 4 h / -30 - 20 °C 7.1: AcOH; H2O / tetrahydrofuran / 24 h / 20 °C 8.1: NaBH4 / methanol 9.1: CBr4; PPh3 / acetonitrile / 0 °C 9.2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / -40 °C 10.1: tetrahydrofuran / -78 °C 11.1: LiHMDS / tetrahydrofuran / -78 °C 11.2: 80 percent / tetrahydrofuran 12.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 12.2: 85 percent / nBu4NF / tetrahydrofuran 13.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 13.2: 60 percent / DMAP / toluene / 80 °C 14.1: 86 percent / TFA / CH2Cl2 / 0 °C 15.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme

1.1: various solvent(s) / 1 h / 240 °C 2.1: TsOH; MeOH / CH2Cl2 3.1: Et3N; DMAP / CH2Cl2 4.1: Pd(OAc)2; DPPP; Bu4NOAc / 1 h / 20 °C 4.2: NaBH4 4.3: NaOMe; MeOH 5.1: (COCl)2; DMSO; Et3N 6.1: tetrahydrofuran / -78 - 20 °C 7.1: (COCl)2; DMSO; Et3N / CH2Cl2 8.1: tBuOK / tetrahydrofuran 8.2: 75 percent / tetrahydrofuran / 4 h / -30 - 20 °C 9.1: AcOH; H2O / tetrahydrofuran / 24 h / 20 °C 10.1: NaBH4 / methanol 11.1: CBr4; PPh3 / acetonitrile / 0 °C 11.2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / -40 °C 12.1: tetrahydrofuran / -78 °C 13.1: LiHMDS / tetrahydrofuran / -78 °C 13.2: 80 percent / tetrahydrofuran 14.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 14.2: 85 percent / nBu4NF / tetrahydrofuran 15.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 15.2: 60 percent / DMAP / toluene / 80 °C 16.1: 86 percent / TFA / CH2Cl2 / 0 °C 17.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme

1.1: NMO; OsO4 / 2-methyl-propan-2-ol; H2O 2.1: H5IO6 3.1: tetrahydrofuran 4.1: NMO; TPAP; mol sieves 4 Angstroem / acetonitrile 5.1: NMO; OsO4 / 2-methyl-propan-2-ol; H2O 6.1: H5IO6 7.1: tetrahydrofuran / 0.5 h / -78 °C 8.1: iPr2NEt / CH2Cl2 / -78 °C 9.1: PPTS / ethanol / 20 °C 10.1: 96 percent / NMO; TPAP; mol sieves 4 Angstroem / acetonitrile 11.1: LiHMDS / tetrahydrofuran / -78 °C 11.2: 80 percent / tetrahydrofuran 12.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 12.2: 85 percent / nBu4NF / tetrahydrofuran 13.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 13.2: 60 percent / DMAP / toluene / 80 °C 14.1: 86 percent / TFA / CH2Cl2 / 0 °C 15.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme

1.1: tetrahydrofuran 2.1: NMO; TPAP; mol sieves 4 Angstroem / acetonitrile 3.1: NMO; OsO4 / 2-methyl-propan-2-ol; H2O 4.1: H5IO6 5.1: tetrahydrofuran / 0.5 h / -78 °C 6.1: iPr2NEt / CH2Cl2 / -78 °C 7.1: PPTS / ethanol / 20 °C 8.1: 96 percent / NMO; TPAP; mol sieves 4 Angstroem / acetonitrile 9.1: LiHMDS / tetrahydrofuran / -78 °C 9.2: 80 percent / tetrahydrofuran 10.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 10.2: 85 percent / nBu4NF / tetrahydrofuran 11.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 11.2: 60 percent / DMAP / toluene / 80 °C 12.1: 86 percent / TFA / CH2Cl2 / 0 °C 13.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme

1.1: tBuOK / tetrahydrofuran 1.2: 75 percent / tetrahydrofuran / 4 h / -30 - 20 °C 2.1: AcOH; H2O / tetrahydrofuran / 24 h / 20 °C 3.1: NaBH4 / methanol 4.1: CBr4; PPh3 / acetonitrile / 0 °C 4.2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / -40 °C 5.1: tetrahydrofuran / -78 °C 6.1: LiHMDS / tetrahydrofuran / -78 °C 6.2: 80 percent / tetrahydrofuran 7.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 7.2: 85 percent / nBu4NF / tetrahydrofuran 8.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 8.2: 60 percent / DMAP / toluene / 80 °C 9.1: 86 percent / TFA / CH2Cl2 / 0 °C 10.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme

1.1: (COCl)2; DMSO; Et3N / CH2Cl2 2.1: tBuOK / tetrahydrofuran 2.2: 75 percent / tetrahydrofuran / 4 h / -30 - 20 °C 3.1: AcOH; H2O / tetrahydrofuran / 24 h / 20 °C 4.1: NaBH4 / methanol 5.1: CBr4; PPh3 / acetonitrile / 0 °C 5.2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / -40 °C 6.1: tetrahydrofuran / -78 °C 7.1: LiHMDS / tetrahydrofuran / -78 °C 7.2: 80 percent / tetrahydrofuran 8.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 8.2: 85 percent / nBu4NF / tetrahydrofuran 9.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 9.2: 60 percent / DMAP / toluene / 80 °C 10.1: 86 percent / TFA / CH2Cl2 / 0 °C 11.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme

1.1: Pd(OAc)2; DPPP; Bu4NOAc / 1 h / 20 °C 1.2: NaBH4 1.3: NaOMe; MeOH 2.1: (COCl)2; DMSO; Et3N 3.1: tetrahydrofuran / -78 - 20 °C 4.1: (COCl)2; DMSO; Et3N / CH2Cl2 5.1: tBuOK / tetrahydrofuran 5.2: 75 percent / tetrahydrofuran / 4 h / -30 - 20 °C 6.1: AcOH; H2O / tetrahydrofuran / 24 h / 20 °C 7.1: NaBH4 / methanol 8.1: CBr4; PPh3 / acetonitrile / 0 °C 8.2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / -40 °C 9.1: tetrahydrofuran / -78 °C 10.1: LiHMDS / tetrahydrofuran / -78 °C 10.2: 80 percent / tetrahydrofuran 11.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 11.2: 85 percent / nBu4NF / tetrahydrofuran 12.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 12.2: 60 percent / DMAP / toluene / 80 °C 13.1: 86 percent / TFA / CH2Cl2 / 0 °C 14.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme

1.1: AcOH; H2O / tetrahydrofuran / 24 h / 20 °C 2.1: NaBH4 / methanol 3.1: CBr4; PPh3 / acetonitrile / 0 °C 3.2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / -40 °C 4.1: tetrahydrofuran / -78 °C 5.1: LiHMDS / tetrahydrofuran / -78 °C 5.2: 80 percent / tetrahydrofuran 6.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 6.2: 85 percent / nBu4NF / tetrahydrofuran 7.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 7.2: 60 percent / DMAP / toluene / 80 °C 8.1: 86 percent / TFA / CH2Cl2 / 0 °C 9.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme

1.1: CBr4; PPh3 / acetonitrile / 0 °C 1.2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / -40 °C 2.1: tetrahydrofuran / -78 °C 3.1: LiHMDS / tetrahydrofuran / -78 °C 3.2: 80 percent / tetrahydrofuran 4.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 4.2: 85 percent / nBu4NF / tetrahydrofuran 5.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 5.2: 60 percent / DMAP / toluene / 80 °C 6.1: 86 percent / TFA / CH2Cl2 / 0 °C 7.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme