Multi-step reaction with 11 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 - 0 °C
2.1: ozone / dichloromethane / -78 °C
2.2: -78 - 20 °C
3.1: chloro-trimethyl-silane; titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h / 0 °C
4.1: pyridine; trifluoroacetyl chloride / dichloromethane / 8 h / 20 °C
5.1: dihydrogen peroxide; sodium hydroxide / methanol; dichloromethane; water / 0 °C
6.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / 1.17 h / 0 °C
7.1: pyridine / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere
8.1: tetrabutylammoniun azide / toluene / 72 h / 20 °C / Molecular sieve; Inert atmosphere
9.1: water; trifluoroacetic acid / acetonitrile / 4 h / 0 °C / Inert atmosphere
10.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C
11.1: tetrahydrofuran; diethyl ether / 3 h / -78 °C / Inert atmosphere
With
pyridine; sodium tetrahydroborate; chloro-trimethyl-silane; oxalyl dichloride; cerium(III) chloride heptahydrate; water; dihydrogen peroxide; tetrabutylammoniun azide; titanium tetrachloride; Dess-Martin periodane; ozone; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trifluoroacetyl chloride; sodium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile;
6.1: Luche reduction;
DOI:10.1002/anie.201008079