Multi-step reaction with 18 steps
1: 95.6 percent / tetrahydrofuran / 0.17 h / ice-cooling
2: 1) Et3N, ethyl chloroformate, 2) NaN3 / 1) acetone, ice-cooling, 0.5 h, 2) acetone, water, ice-cooling, 1 h
3: 16 h / Heating
4: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature
5: Et3N / CHCl3 / 1 h / Ambient temperature
6: 100 percent / N-methylmorpholine N-oxide / OsO4 / dioxane / 2 h / Ambient temperature
7: 92.7 percent / pyridine / DMAP / 2 h / Ambient temperature
8: 1) t-BuOK / 1) THF, room temperature, 0.5 h, 2) room temperature, 2 h
9: 1) BH3*THF, 2) 3 M aq. NaOH, 30percent aq. H2O2 / 1) THF, ice-cooling, 4 h, 2) water, room temperature, 40 min
10: 100 percent / pyridine / 1 h / Ambient temperature
11: 80.6 percent / methanesulfonic acid, Ac2O / 1,2-dichloro-ethane / 2 h / Ambient temperature
12: 100 percent / NaOMe / methanol / 0.33 h / Ambient temperature
13: 82.5 percent / p-TsOH*H2O / CHCl3 / 1.33 h / Ambient temperature
14: 90.7 percent / sodium bis(2-methoxyethoxy)aluminum hydride / o-xylene / 0.58 h / Heating
15: 74.6 percent / diisobutylaluminum hydride / toluene / 2 h / Ambient temperature
16: 100 percent / Et3N / CH2Cl2 / 0.17 h / ice-cooling
17: 33 percent / DBU / o-xylene / 2.5 h / Ambient temperature
18: 1) PhSeCl, 2) NaIO4 / 1) MeOH, 15-20 deg C, sonication, 2 h, 2) H2O, 10 min
With
pyridine; sodium hydroxide; sodium periodate; sodium azide; Phenylselenyl chloride; borane-THF; methanesulfonic acid; potassium tert-butylate; dihydrogen peroxide; sodium methylate; chloroformic acid ethyl ester; acetic anhydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid;
dmap; osmium(VIII) oxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; o-xylene; 1,2-dichloro-ethane; toluene;
DOI:10.1021/jo00052a051
