Multi-step reaction with 19 steps
1: 84 percent / NaH, TBAI / tetrahydrofuran / 0 - 20 °C
2: N-methylmorpholine N-oxide, OsO4, H2O / tetrahydrofuran
3: aq. NaIO4 / methanol / 0 - 20 °C
4: toluene / -78 °C
5: 2,6-lutidine / CH2Cl2 / 0 - 20 °C
6: Li, NH3 / tetrahydrofuran / -78 °C
7: Et3N / diethyl ether
8: hydrogen fluoride pyridine complex, pyridine / tetrahydrofuran
9: 92 percent / KOH / methanol
10: 87 percent / BuLi / -78 - 20 °C
11: 85 percent / Li, NH3 / tetrahydrofuran / -78 °C
12: N-methylmorpholine N-oxide, OsO4, H2O / tetrahydrofuran
13: aq. NaIO4 / methanol / 0 - 20 °C
14: 1.) diketene acetone adduct, Et3N / 1.) hexane, 70 deg C, 2.) 125 deg C, 0.2 Torr
15: 1.) tert-BuLi, Bu3SnCl, 2.) NIS, K2CO3 / 1.) THF, -78 to -30 deg C; -78 to 20 deg C, 2.) 0 deg C
16: 1.) tert-BuLi, MgBr2 / 1.) Et2O, -78 deg C, 2.) -78 to -50 deg C
17: 1.) NIS, CaCO3, 2.) Bu3SnH, AIBN / 1.) MeOH, THF, CH3CN, 0-20 deg C, 2.) THF, PhBr, 80 deg C
18: 76 percent / TBAF / tetrahydrofuran
19: 75 percent / imidazole / dimethylformamide
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; potassium hydroxide; sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); diketene acetone; tributyltin chloride; tetrabutyl ammonium fluoride; ammonia; water; tert.-butyl lithium; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; potassium carbonate; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; calcium carbonate; magnesium bromide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/(sici)1521-3773(19980202)37:1/2<190::aid-anie190>3.0.co;2-0