Multi-step reaction with 8 steps
1.1: oxalyl chloride; DMF / benzene / 1 h / Heating
1.2: 92 percent / triethylamine / CH2Cl2 / 1.2 h / 0 - 20 °C
2.1: hydrogen / Pd-C / methanol / 4 h / 2068.59 Torr
3.1: 4.88 g / sodium bicarbonate / dimethylformamide / 20 °C
4.1: 100 percent / N-methylmorpholine N-oxide / osmium tetroxide / H2O; acetone; 2-methyl-propan-2-ol / 20 °C
5.1: 85 percent / p-toluenesulfonic acid / acetone / 48 h
6.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C
6.2: 42 percent / 4-nitrobenzenesulfonyl azide / tetrahydrofuran / -78 - 20 °C
7.1: 4 Angstroem molecular sieves / copper(I) triflate; 2,2-bis[(S)-4-isopropyl-2-oxazolin-2-yl]propane / CHCl3 / 12 h
8.1: 82 mg / DDQ / CH2Cl2 / 1 h
With
oxalyl dichloride; 4 A molecular sieve; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; N,N-dimethyl-formamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium on activated charcoal; osmium(VIII) oxide; copper(I) triflate; 2,2-bis[(4S)-4-isopropyloxazolin-2-yl]propane;
In
tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
1.1: Condensation / 1.2: Esterification / 2.1: Hydrogenation / 3.1: Cyclization / 4.1: Oxidation / 5.1: Cyclization / 6.1: Metallation / 6.2: diazo transfer / 7.1: Cyclization / 8.1: Oxidation;
DOI:10.1016/S0040-4020(97)01033-8