Multi-step reaction with 13 steps
1: 50 percent / (Ph3P)3RhCl / toluene; acetonitrile / 2.5 h / Heating
2: 1.) LDA / 1.) Et2O, -78 deg C, 1 h; 2.) -78 deg C, 10 min
3: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature
4: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
5: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
6: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
7: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
8: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
9: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
10: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
11: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
12: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
13: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
With
hydrogenchloride; Wilkinson's catalyst; titanium(III) chloride; oxalyl dichloride; 2-Methoxypropene; Celite; hydrogen fluoride; tetrabutyl ammonium fluoride; L-Selectride; ozone; triethylamine; diisopropylamine; triphenylphosphine; silver carbonate; lithium diisopropyl amide;
dmap; pyridinium p-toluenesulfonate;
In
tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ja00228a067