Multi-step reaction with 11 steps
1: p-TsOH / methanol; CH2Cl2 / 12 h / Ambient temperature
2: 74 percent / pyridine, Ph3P, CI4 / 12 h / Ambient temperature
3: 95percent NaH / dimethylformamide / 20 h
4: 1.) aq. HgCl2, 2.) MsCl, DMAP, pyridine / 1.) acetone, 100 deg C, 1.5 h, 2.) r.t., 4 h
5: 1.) CeCl3*7H2O, 2.) NaBH4 / 1.) MeOH, -50 deg C, 10 min, 2.) -50 deg C, 5 h
6: 55percent m-CPBA / CH2Cl2 / 24 h / Ambient temperature
7: 75 percent / BF3*Et2O / CH2Cl2 / 3.5 h / Ambient temperature
8: 85 percent / Bu2SnO, 3 Angstroem molecular sieves, Bu4NBr / acetonitrile / 5 h / 80 °C
9: 89 percent / PCC / CH2Cl2 / 13 h / Ambient temperature
10: 1.) (R)-Alpine hydride, 2.) 3 M aq. NaOH, 30percent aq. H2O2 / 1.) THF, -90 deg C, 30 min, 2.) O deg C, 30 min
11: 1.) tetrazole, 2.) aq. NaIO4 / 2.) RuCl3*3H2O / 1.) MeCN, CH2Cl2, r.t., 1.5 h, 2.) 0 deg C, 0.5 h
With
pyridine; 1H-tetrazole; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; R-Alpine-Hydride; carbon tetraiodide; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutylammomium bromide; dihydrogen peroxide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; mercury dichloride;
ruthenium trichloride;
In
methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00090a035