Multi-step reaction with 18 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C
1.2: 1.5 h / -78 - 20 °C
2.1: titanium tetrachloride / dichloromethane / -15 °C
2.2: 0.5 h / -15 °C
2.3: 1 h / -15 °C
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
4.1: sodium tetrahydroborate; methanol / 1 h
5.1: triphenylphosphine; carbon tetrabromide / acetonitrile / 2.08 h / 0 - 20 °C
6.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -45 - 30 °C
6.2: 5 h / -40 - 0 °C
7.1: boron trifluoride diethyl etherate; ethane-1,2-dithiol / dichloromethane / 0.5 h / -20 °C
8.1: sodium bis(2-methoxyethoxy)aluminium dihydride / 4 h / 0 - 20 °C
9.1: diethyl (2R,3R)-tartrate; titanium(IV) isopropylate / dichloromethane / 0.5 h / -20 °C / Molecular sieve
9.2: 8 h / -20 °C
10.1: pyridine; Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C
11.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C
11.2: 0.33 h / -78 °C
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C
13.1: sodium hydride / tetrahydrofuran; dimethyl sulfoxide / 2 h / 20 °C
14.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Inert atmosphere
15.1: ozone; dimethylsulfide / dichloromethane / 0.08 h
16.1: sodium tetrahydroborate; methanol / 1 h / 0 °C
17.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.08 h / 0 °C
17.2: 3 h / 20 °C
18.1: triphenylphosphine; water / tetrahydrofuran / 4 h / 0 °C
With
pyridine; titanium(IV) isopropylate; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; dimethylsulfide; diethyl (2R,3R)-tartrate; carbon tetrabromide; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; titanium tetrachloride; sodium hydride; Dess-Martin periodane; ozone; ethane-1,2-dithiol; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile;
9.1: |Sharpless Asymmetric Epoxidation / 9.2: |Sharpless Asymmetric Epoxidation;
DOI:10.1016/j.tetlet.2013.01.134