Multi-step reaction with 13 steps
1: AgClO4, SnCl2, molecular sieves (4 Angstroem) / tetrahydrofuran / 7 h / -78 - -20 °C
2: NaH / tetrahydrofuran; ethane-1,2-diol / 0.5 h / 25 °C
3: 1.) n-Bu2SnO, 2.) n-Bu3SnOMe, Br2 / 1.) MeOH, reflux, 1.2 h, 2.) CH2Cl2, 25 deg C
4: 70 percent / pyridinium p-toluenesulfonate / benzene / 3 h / 25 °C
5: 100 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 to 25 deg C
6: 95 percent / i-Bu2AlH / CH2Cl2 / 0.5 h / -78 °C
7: 86 percent / acetonitrile / 1.5 h / 25 °C
8: 100 percent / toluene / 1 h / 100 °C
9: 95 percent / NaSMe, EtSH / CH2Cl2 / 1.5 h / 25 °C
10: 90 percent / i-Pr2EtN / CH2Cl2 / 1 h / 25 °C
11: 1.) AcOH, n-Bu4NF, 2.) K-Selectride / 1.) THF, -40 to 0 deg C, 2.) DME, THF, -78 deg C, 0.7 h
12: 85 percent / HF*py / CH2Cl2; tetrahydrofuran / 3 h / -20 - 0 °C
13: NaBH3CN, BF3*OEt2 / CH2Cl2; tetrahydrofuran; diethyl ether / 2 h / -60 - -40 °C
With
2,6-dimethylpyridine; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; bromine; tributyltin methoxide; silver perchlorate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; potassium tri-sec-butyl-borohydride; pyridine hydrogenfluoride; acetic acid; N-ethyl-N,N-diisopropylamine; ethanethiol; tin(ll) chloride; sodium thiomethoxide;
In
tetrahydrofuran; diethyl ether; dichloromethane; ethylene glycol; toluene; acetonitrile; benzene;