Multi-step reaction with 9 steps
1: 1.) NaH, 2.) TosN3 / 1.) benzene, THF, 0 deg C, 1.5 h, 2.) benzene, THF, RT, 3 h
2: 58 percent / dirhodium(II) tetraacetate / CH2Cl2 / 2 h / Heating
3: 1.) O3, 2.) Me2S / 1.) MeOH, -70 deg C, 2.) MeOH, from -10 deg C to RT, 3 h
4: CrO3, aq. H2SO4 / acetone / 0.5 h
5: diethyl ether / 0.5 h / Ambient temperature
6: H20, phosphate buffer, α-chymotrypsin
7: 1.) NaH / 1.) THF, RT, 1.5 h, 2.) THF, 40 deg C, 1 h
8: H2 / 10percent Pd/C / methanol / 0.33 h / 760 Torr
9: diethyl ether / 0 °C
With
chromium(VI) oxide; dirhodium tetraacetate; 4-toluenesulfonyl azide; phosphate buffer; dimethylsulfide; sulfuric acid; water; hydrogen; sodium hydride; ozone; α-chymotrypsin;
palladium on activated charcoal;
In
methanol; diethyl ether; dichloromethane; acetone;
DOI:10.1055/s-1997-1193