sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene in water; tert-butyl alcohol T=20°C;

Acylation;

1.1: DPPA; Et3N / toluene / 1 h / Heating 1.2: 72 percent / toluene / 1 h / Heating 2.1: O3 / CH2Cl2 / 0.07 h / -78 °C 2.2: Me2S / CH2Cl2 / -78 - 20 °C 3.1: 21 mg / 2-methyl-2-butene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 20 °C View Scheme

1.1: DPPA; Et3N / toluene / 1 h / Heating 1.2: 72 percent / toluene / 1 h / Heating 2.1: O3 / CH2Cl2 / 0.07 h / -78 °C 2.2: Me2S / CH2Cl2 / -78 - 20 °C 3.1: 21 mg / 2-methyl-2-butene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 20 °C View Scheme

1.1: 100 percent / Jones reagent / acetone / 2 h / 0 °C 2.1: DPPA; Et3N / toluene / 1 h / Heating 2.2: 72 percent / toluene / 1 h / Heating 3.1: O3 / CH2Cl2 / 0.07 h / -78 °C 3.2: Me2S / CH2Cl2 / -78 - 20 °C 4.1: 21 mg / 2-methyl-2-butene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 20 °C View Scheme

1.1: O3 / CH2Cl2 / 0.07 h / -78 °C 1.2: Me2S / CH2Cl2 / -78 - 20 °C 2.1: 21 mg / 2-methyl-2-butene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 20 °C View Scheme

1: molecular sieves 4A / toluene / 1 h / 0 °C 2: (R)-1,1'-binaphthyl-3,3'-bis(Ph2P=O)-2,2'-diyl-AlCl; PhOH / CH2Cl2 / 44 h / -40 °C 3: MnO2 / CH2Cl2 / 1 h / 20 °C 4: 1 N aq. HCl / tetrahydrofuran / 1 h / 20 °C 5: aq. HCl / 24 h / 120 °C 6: K2CO3 / H2O; acetone / 4 h / 20 °C View Scheme

1: MnO2 / CH2Cl2 / 1 h / 20 °C 2: 1 N aq. HCl / tetrahydrofuran / 1 h / 20 °C 3: aq. HCl / 24 h / 120 °C 4: K2CO3 / H2O; acetone / 4 h / 20 °C View Scheme

1: 1 N aq. HCl / tetrahydrofuran / 1 h / 20 °C 2: aq. HCl / 24 h / 120 °C 3: K2CO3 / H2O; acetone / 4 h / 20 °C View Scheme