Multi-step reaction with 7 steps
1: 85 percent / 0.1 N KOH / methanol
2: 1.) BF3*Et2O / 1.) -78 deg C, 2.) THF, -78 deg C
3: 1.) OsO4, pyridine, 2.) 10percent aq. NaHSO3, pyridine / 1.) RT, 2.) RT
4: 73 percent / SOCl2, pyridine / tetrahydrofuran / 1.) 0 deg C, 2.5 h, 2.) 5 deg C, overnight
5: 90 percent / DMAP / CH2Cl2 / 1 h / 40 °C
6: aq. AcOH / tetrahydrofuran / 1 h / 50 °C
7: 1.) m-CPBA, 2.) aq. HIO4 / 1.) CH2Cl2, RT, 1 h, 2.) dioxane, RT, 16 h
With
pyridine; dmap; potassium hydroxide; osmium(VIII) oxide; thionyl chloride; boron trifluoride diethyl etherate; sodium hydrogensulfite; acetic acid; periodic acid; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.3987/COM-90-5656