Multi-step reaction with 14 steps
1: 84 percent / PCl3 / CHCl3 / 40 h / Ambient temperature
2: 50 percent / NaOH / dimethylsulfoxide / 0.5 h / 15 - 20 °C
3: 83 percent / methanol / Ambient temperature
4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, then -78 to 0 deg C, 45 min, 2.) THF, hexane, 1.25 h
5: 94 percent / Na/Hg, Na2HPO4 / methanol / 2.5 h / Ambient temperature
6: 89 percent / OsO4, NaIO4 / tetrahydrofuran / 7 h / 0 - 20 °C
7: 81 percent / tetrahydrofuran / 4.5 h / -50 - 20 °C
8: 95 percent / Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6.5 h / Ambient temperature
9: 97 percent / m-CPBA / CH2Cl2 / 3 h / Ambient temperature
10: 1.) p-TsCl, Et3N / 1.) CH2Cl2, -50 deg C, 5 h, 2.) DMF, room temp., 12 h
11: 1.) NaHMDS, 2.) Pd2(dba)3*CHCl3, 1,2-bis(diphenylphosphino)ethane / 1.) THF, -78 deg C, 70 min, 2.) THF, reflux, 4 h
12: 66 percent / Na/Hg, Na2HPO4 / methanol / 2 h / Ambient temperature
13: 100 percent / n-Bu4NF / tetrahydrofuran / 5.5 h / 0 °C
14: 98 percent / Et3N, 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 50 h / Ambient temperature
With
dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium hydroxide; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; 1,2-bis-(diphenylphosphino)ethane; phosphorus trichloride;
In
tetrahydrofuran; methanol; dichloromethane; chloroform; dimethyl sulfoxide;
DOI:10.1021/jo9801770