Multi-step reaction with 11 steps
1.1: 15.74 g / Et3N; DBU / CH2Cl2
2.1: tert-butyllithium / tetrahydrofuran; pentane / 0.5 h / -78 °C
2.2: 99 percent / tetrahydrofuran; pentane / 3 h / -78 °C
3.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.33 h / 0 °C
3.2: 88 percent / tetrahydrofuran / -78 - -30 °C
4.1: tert-butyllithium / diethyl ether; pentane / 0.03 h / -78 °C
4.2: 96 percent / diethyl ether; pentane / 3.5 h / -78 - 0 °C
5.1: potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran; toluene / 1.48 h / -78 - -40 °C
5.2: 81 percent / tetrahydrofuran; toluene / 3 h / -78 °C
6.1: 54 percent / NMO*H2O; osmium tetraoxide; water / acetone / 120 h / 0 °C
7.1: pyridine / CH2Cl2; toluene / 0.25 h / -78 °C
8.1: 890 mg / methanol; Dowex 50X4-400 / 2.5 h
9.1: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 2.33 h / -78 - 20 °C
10.1: 12 percent / aq. sodium hydroxide / methanol; tetrahydrofuran
11.1: 78 percent / DDQ; 4 Angstroem molecular sieves / diethyl ether / 6 h / 20 °C
With
pyridine; methanol; sodium hydroxide; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; 4 A molecular sieve; Dowex 50X4-400; water; tert.-butyl lithium; sodium hexamethyldisilazane; potassium hexamethylsilazane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; pentane;
3.2: Wittig condensation / 9.1: Swern oxidation;
DOI:10.1021/jo020627v