Multi-step reaction with 7 steps
1: NaOH / H2O / 0.5 h / 25 °C
2: Et3N / diethyl ether / 1 h / 0 °C
3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, a) -78 deg C, 15 min, b) 0 deg C, 30 min
4: 1.) TiCl4, diisopropylethylamine, 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, 3 h, 2.) CH2Cl2, 25 deg C, 2 h
5: 93 percent / LiBH4 / methanol; tetrahydrofuran / 0.67 h / 0 °C
6: 1.) oxalyl chloride, DMSO, 2.) diisopropylethylamine / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, -50 deg C, 1 h
7: 1.) Sn(OTf)2, Et3N, 2.) TMEDA
With
sodium hydroxide; lithium borohydride; tin(II) trifluoromethanesulfonate; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; titanium tetrachloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; diethyl ether; water;
DOI:10.1021/ja00050a024