1: 1.) O3, 2.) Me2S / 1.) EtOAc, -40 deg C, 6.5 h, 2.) EtOAc, from -40 deg C to RT 2: 91 percent / pyridinium tosylate / benzene / 0.25 h / Heating 3: 1.) KMnO4, 2.) Pb(OAc)4 / 1.) a) tert-BuOH, H2O, RT, 40 min, b) tert-BuOH, H2O, 40 deg C, 10 min, 2.) MeOH, RT, 1h 4: 82 percent / m-CPBA / CH2Cl2 / 12 h / Heating 5: 100 percent / KOH, EtOH / 0.5 h 6: FeCl3 / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 24 h 7: 384 mg / sodium acetate / methanol / 3 h / Heating 8: 70 percent / CuI / tetrahydrofuran; various solvent(s) / 1 h 9: 1.) LDA / 1.) dimethoxyethane, -40 deg C, 2.) dimethoxyethane, 50 deg C, 30 min 10: 1.) LDA, 2.) phenylselenyl chloride, 3.) pyridine, 30percent H2O2 11: 90 percent / NH3, Li / tetrahydrofuran / 1 h / -33 °C 12: 95 percent / L-Selectride / tetrahydrofuran / 2.5 h / -78 - 0 °C 13: 1.) BH3, 2.) 30percent aq. H2O2, aq. NaOH / 1.) THF, 0 deg C to RT, 1.5 h, 2.) THF, water, overnight 14: 48 percent / p-toluenesulfonic acid / toluene / 2 h / 80 °C View Scheme

1: 62 percent / KOH, hydrazine / bis-(2-hydroxy-ethyl) ether / 1.) 100 deg C, 1.5 h, 2.) 210 deg C, 4 h 2: 1.) O3, 2.) Me2S / 1.) EtOAc, -40 deg C, 6.5 h, 2.) EtOAc, from -40 deg C to RT 3: 91 percent / pyridinium tosylate / benzene / 0.25 h / Heating 4: 1.) KMnO4, 2.) Pb(OAc)4 / 1.) a) tert-BuOH, H2O, RT, 40 min, b) tert-BuOH, H2O, 40 deg C, 10 min, 2.) MeOH, RT, 1h 5: 82 percent / m-CPBA / CH2Cl2 / 12 h / Heating 6: 100 percent / KOH, EtOH / 0.5 h 7: FeCl3 / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 24 h 8: 384 mg / sodium acetate / methanol / 3 h / Heating 9: 70 percent / CuI / tetrahydrofuran; various solvent(s) / 1 h 10: 1.) LDA / 1.) dimethoxyethane, -40 deg C, 2.) dimethoxyethane, 50 deg C, 30 min 11: 1.) LDA, 2.) phenylselenyl chloride, 3.) pyridine, 30percent H2O2 12: 90 percent / NH3, Li / tetrahydrofuran / 1 h / -33 °C 13: 95 percent / L-Selectride / tetrahydrofuran / 2.5 h / -78 - 0 °C 14: 1.) BH3, 2.) 30percent aq. H2O2, aq. NaOH / 1.) THF, 0 deg C to RT, 1.5 h, 2.) THF, water, overnight 15: 48 percent / p-toluenesulfonic acid / toluene / 2 h / 80 °C View Scheme

toluene-4-sulfonic acid in dichloromethane

toluene-4-sulfonic acid in dichloromethane 30 h; Heating; Title compound not separated from byproducts;

1: 70 percent / CuI / tetrahydrofuran; various solvent(s) / 1 h 2: 1.) LDA / 1.) dimethoxyethane, -40 deg C, 2.) dimethoxyethane, 50 deg C, 30 min 3: 1.) LDA, 2.) phenylselenyl chloride, 3.) pyridine, 30percent H2O2 4: 90 percent / NH3, Li / tetrahydrofuran / 1 h / -33 °C 5: 95 percent / L-Selectride / tetrahydrofuran / 2.5 h / -78 - 0 °C 6: 1.) BH3, 2.) 30percent aq. H2O2, aq. NaOH / 1.) THF, 0 deg C to RT, 1.5 h, 2.) THF, water, overnight 7: 48 percent / p-toluenesulfonic acid / toluene / 2 h / 80 °C View Scheme

1: FeCl3 / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 24 h 2: 384 mg / sodium acetate / methanol / 3 h / Heating 3: 70 percent / CuI / tetrahydrofuran; various solvent(s) / 1 h 4: 1.) LDA / 1.) dimethoxyethane, -40 deg C, 2.) dimethoxyethane, 50 deg C, 30 min 5: 1.) LDA, 2.) phenylselenyl chloride, 3.) pyridine, 30percent H2O2 6: 90 percent / NH3, Li / tetrahydrofuran / 1 h / -33 °C 7: 95 percent / L-Selectride / tetrahydrofuran / 2.5 h / -78 - 0 °C 8: 1.) BH3, 2.) 30percent aq. H2O2, aq. NaOH / 1.) THF, 0 deg C to RT, 1.5 h, 2.) THF, water, overnight 9: 48 percent / p-toluenesulfonic acid / toluene / 2 h / 80 °C View Scheme

1: 91 percent / pyridinium tosylate / benzene / 0.25 h / Heating 2: 1.) KMnO4, 2.) Pb(OAc)4 / 1.) a) tert-BuOH, H2O, RT, 40 min, b) tert-BuOH, H2O, 40 deg C, 10 min, 2.) MeOH, RT, 1h 3: 82 percent / m-CPBA / CH2Cl2 / 12 h / Heating 4: 100 percent / KOH, EtOH / 0.5 h 5: FeCl3 / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 24 h 6: 384 mg / sodium acetate / methanol / 3 h / Heating 7: 70 percent / CuI / tetrahydrofuran; various solvent(s) / 1 h 8: 1.) LDA / 1.) dimethoxyethane, -40 deg C, 2.) dimethoxyethane, 50 deg C, 30 min 9: 1.) LDA, 2.) phenylselenyl chloride, 3.) pyridine, 30percent H2O2 10: 90 percent / NH3, Li / tetrahydrofuran / 1 h / -33 °C 11: 95 percent / L-Selectride / tetrahydrofuran / 2.5 h / -78 - 0 °C 12: 1.) BH3, 2.) 30percent aq. H2O2, aq. NaOH / 1.) THF, 0 deg C to RT, 1.5 h, 2.) THF, water, overnight 13: 48 percent / p-toluenesulfonic acid / toluene / 2 h / 80 °C View Scheme

1: 1.) KMnO4, 2.) Pb(OAc)4 / 1.) a) tert-BuOH, H2O, RT, 40 min, b) tert-BuOH, H2O, 40 deg C, 10 min, 2.) MeOH, RT, 1h 2: 82 percent / m-CPBA / CH2Cl2 / 12 h / Heating 3: 100 percent / KOH, EtOH / 0.5 h 4: FeCl3 / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 24 h 5: 384 mg / sodium acetate / methanol / 3 h / Heating 6: 70 percent / CuI / tetrahydrofuran; various solvent(s) / 1 h 7: 1.) LDA / 1.) dimethoxyethane, -40 deg C, 2.) dimethoxyethane, 50 deg C, 30 min 8: 1.) LDA, 2.) phenylselenyl chloride, 3.) pyridine, 30percent H2O2 9: 90 percent / NH3, Li / tetrahydrofuran / 1 h / -33 °C 10: 95 percent / L-Selectride / tetrahydrofuran / 2.5 h / -78 - 0 °C 11: 1.) BH3, 2.) 30percent aq. H2O2, aq. NaOH / 1.) THF, 0 deg C to RT, 1.5 h, 2.) THF, water, overnight 12: 48 percent / p-toluenesulfonic acid / toluene / 2 h / 80 °C View Scheme

1: 1.) LDA / 1.) dimethoxyethane, -40 deg C, 2.) dimethoxyethane, 50 deg C, 30 min 2: 1.) LDA, 2.) phenylselenyl chloride, 3.) pyridine, 30percent H2O2 3: 90 percent / NH3, Li / tetrahydrofuran / 1 h / -33 °C 4: 95 percent / L-Selectride / tetrahydrofuran / 2.5 h / -78 - 0 °C 5: 1.) BH3, 2.) 30percent aq. H2O2, aq. NaOH / 1.) THF, 0 deg C to RT, 1.5 h, 2.) THF, water, overnight 6: 48 percent / p-toluenesulfonic acid / toluene / 2 h / 80 °C View Scheme

1: 82 percent / m-CPBA / CH2Cl2 / 12 h / Heating 2: 100 percent / KOH, EtOH / 0.5 h 3: FeCl3 / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 24 h 4: 384 mg / sodium acetate / methanol / 3 h / Heating 5: 70 percent / CuI / tetrahydrofuran; various solvent(s) / 1 h 6: 1.) LDA / 1.) dimethoxyethane, -40 deg C, 2.) dimethoxyethane, 50 deg C, 30 min 7: 1.) LDA, 2.) phenylselenyl chloride, 3.) pyridine, 30percent H2O2 8: 90 percent / NH3, Li / tetrahydrofuran / 1 h / -33 °C 9: 95 percent / L-Selectride / tetrahydrofuran / 2.5 h / -78 - 0 °C 10: 1.) BH3, 2.) 30percent aq. H2O2, aq. NaOH / 1.) THF, 0 deg C to RT, 1.5 h, 2.) THF, water, overnight 11: 48 percent / p-toluenesulfonic acid / toluene / 2 h / 80 °C View Scheme