Multi-step reaction with 7 steps
1: 1.) N-hydroxyphthalimide, dibenzoyl peroxide, air, 2.) CuCl2 / 1.) EtOAc, acetone, 50 - 55 deg C, 48 h, 2.) pyridine, 0 deg C, overnight
2: 1.) Li, NH3, 2.) NH4Cl / 1.) THF, 1 h, dry ice/acetone bath
3: 96 percent / K-selectride / tetrahydrofuran / -20 °C
4: 92 percent / Ag2CO3/celite / toluene / 8 h
5: 86 percent / DMAP / pyridine / 8 h / 0 - 20 °C
6: 95 percent / p-TsOH / toluene / 2 h / Heating
7: 1.) O3, 2.) (MeO)3P / 1.) Ch2Cl2, EtOH, dry ice/ethanol bath, 2.) warm to room temperature
With
dmap; N-hydroxyphthalimide; air; Celite; ammonia; lithium; potassium tri-sec-butyl-borohydride; ammonium chloride; toluene-4-sulfonic acid; ozone; silver carbonate; copper dichloride; phosphorous acid trimethyl ester; dibenzoyl peroxide;
In
tetrahydrofuran; pyridine; toluene;
DOI:10.1021/jo971405d