Multi-step reaction with 12 steps
1: 71 percent / DMAP / pyridine / 49 h / Ambient temperature
2: 99 percent / DBU / benzene / 0.5 h / Ambient temperature
3: 100 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature
4: 98 percent / Et3N / CH2Cl2 / 0.67 h / 0 °C
5: 85 percent / Na, NH3 / tetrahydrofuran / 1.25 h / -78 °C
6: 72 percent / 4A molecular sieves, p-TSA / CH2Cl2 / 24 h / 20 °C
7: 99 percent / DIBAL / CH2Cl2; hexane / 5 h / Ambient temperature
8: 100 percent / NMO, TPAP / CH2Cl2 / 2 h / 20 °C
9: 1.) Cu(I)CN, 3.) Et3N
10: DDQ / benzene / 2 h / 0 °C
11: 85 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C
12: 100 percent / DMAP / CH2Cl2 / 3.6 h / Ambient temperature
With
dmap; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; ammonia; copper(I) cyanide; sodium; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; pyridine; hexane; dichloromethane; benzene;
DOI:10.1002/ijch.199700004