Multi-step reaction with 15 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / 0 - 20 °C
1.2: 20 °C
2.1: potassium hydroxide / tetrahydrofuran; methanol; water / 70 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
3.2: 1 h / -78 - 20 °C
4.1: dichloromethane / 3 h / 20 °C
5.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 °C
6.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / 2,2,4-trimethylpentane; dichloromethane / 1 h / -40 °C / Molecular sieve
7.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide / dichloromethane; water / 0.17 h / 0 °C
8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C
8.2: 1 h / 0 °C
9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0 - 20 °C
10.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C
10.2: 1 h / 0 - 20 °C
11.1: bis-(1,2-dimethylpropyl)borane / tetrahydrofuran / 3 h / 0 - 20 °C
11.2: 5.5 h / 0 - 20 °C
12.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide / dichloromethane; water / 0.33 h / 0 °C
13.1: diethyl ether / 0.33 h / -78 °C
14.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve
15.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / diethyl ether / 1 h / 0 °C
15.2: -78 - -20 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hypochlorite; tetrapropylammonium perruthennate; oxalyl dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; diethyl (2S,3S)-tartrate; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; sodium hexamethyldisilazane; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium bromide; potassium hydroxide;
In
tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;
3.1: Swern oxidation / 4.1: Wittig reaction / 6.1: Sharpless epoxidation / 8.2: Wittig reaction;
DOI:10.1016/j.tet.2011.05.082