Multi-step reaction with 12 steps
1: 1.) NaH, CS2, MeI, 2.) Bu3SnH, AIBN / 1.) THF, 23 deg C, 2.) toluene, 110 deg C
2: 70 percent / 1N aq. HCl / acetic acid / 60 °C
3: 60 percent / (COCl)2, DMSO / CH2Cl2 / -78 °C
4: tetrahydrofuran / -78 °C
5: Et3SiH, BF3*Et2O / CH2Cl2 / -20 °C
6: 1.) catecholborane, (PPh3)RhCl, 2.) 30percent aq. H2O2, 3 N aq. NaOH / 1.) THF, 23 deg C, 2.) 23 deg C
7: 80 percent / CrO3, H2SO4
8: 85 percent / H2 / Pd(OH)2/C / methanol / 23 °C
9: 90 percent / p-TsOH / dimethylformamide / 50 °C
10: 95 percent / CSA / benzene / 80 °C
11: 1.) n-BuLi, 2.) Et3SiH, BF3*Et2O, 3.) Ph3SnH, BEt3, 4.) NIS, 5.) n-BuLi
12: OsO4, NMO / H2O; acetone; 2-methyl-propan-2-ol / 23 °C
With
chromium(VI) oxide; hydrogenchloride; triethylsilane; carbon disulfide; sodium hydroxide; N-iodo-succinimide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); triethyl borane; (PPh3)RhCl; sulfuric acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; triphenylstannane; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; methyl iodide; benzo[1,3,2]dioxaborole;
palladium dihydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/ja961230+