Multi-step reaction with 7 steps
1.1: 75 percent / DCC; DMAP / CH2Cl2 / 2 h / 20 °C
2.1: 1,4-diazabicyclooctane; butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 39 percent / tetrahydrofuran / -78 - 20 °C
3.1: 60 percent / BF3*Et2O / CH2Cl2 / 0 - 20 °C
4.1: HMDS; butyllithium / tetrahydrofuran; hexane / -78 - 0 °C
4.2: phenylselenenyl chloride / tetrahydrofuran / -78 - 20 °C
4.3: 48 percent / 1,4-diazabicyclooctane; m-chloroperbenzoic acid / tetrahydrofuran; CH2Cl2 / -20 - 20 °C
5.1: 62 percent / CuBr*S(CH3)2; trimethylsilyl chloride / diethyl ether; tetrahydrofuran / -78 - -20 °C
6.1: H2 / Pd/C / ethyl acetate; methanol / 2 h / 3000.24 Torr
7.1: 0.15 g / trifluoroacetic acid / CH2Cl2; H2O / 1 h
With
dmap; n-butyllithium; chloro-trimethyl-silane; 1,4-diazabicyclooctane; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; hydrogen; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate;
DOI:10.1016/S0040-4020(02)01490-4