Multi-step reaction with 10 steps
1.1: 99 percent / imidazole / CH2Cl2 / 3 h
2.1: O3 / CH2Cl2 / -78 °C
2.2: triphenylphosphine / CH2Cl2 / -78 - 20 °C
2.3: 86 percent / CH2Cl2 / 6 h / Heating
3.1: 76 percent / potassium hexamethyldisilazide / tetrahydrofuran / 1.17 h / 0 °C
4.1: zinc(II) triflate; sodium bicarbonate; EtSH / CH2Cl2 / 20 h
5.1: 496 mg / PPTS / CH2Cl2 / 14 h
6.1: 92 percent / MeLi / tetrahydrofuran; diethyl ether / 0.33 h / -78 °C
7.1: diisopropylethylamine; dibutylboron triflate / diethyl ether / 0.5 h / -78 °C
7.2: 78 percent / diethyl ether / 4 h / -109 - -78 °C
8.1: (CH3)4NHB(OAc)3; acetic acid / acetonitrile / 48 h / -25 °C
9.1: 49 mg / PPTS / CH2Cl2 / 14 h / 20 °C
10.1: 90 percent / LiDBB / tetrahydrofuran / 2 h / -78 °C
With
1H-imidazole; lithium 4,4′-di(tert-butyl)biphenyl; di-n-butylboryl trifluoromethanesulfonate; methyllithium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; sodium hydrogencarbonate; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; ethanethiol; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/ja027638q