Multi-step reaction with 12 steps
1.1: 90 percent / Me4NBH(OAc)3; AcOH / acetonitrile / 24 h / 0 °C
2.1: 85 percent / 2,4,6-collidine / CH2Cl2 / 8 h / 5 °C
3.1: 95 percent / Super-Hydride / 1,2-dichloro-ethane; tetrahydrofuran / 0.5 h / 60 °C
4.1: 90 percent / K-10 clay / CH2Cl2 / 4 h / 20 °C
5.1: 70 percent / AsPh3; CuCl; DIEA / Pd2(dba)3 / acetonitrile / 4 h / 70 °C
6.1: 80 percent / Super-Hydride / tetrahydrofuran / 1 h / -78 °C
7.1: Ti(iPrO)4 / CH2Cl2 / 0.5 h / 20 °C
7.2: 60 percent / CH2Cl2 / 10 h / 20 °C
8.1: 140 mg / pyridine / 2 h / 20 °C
9.1: 78 mg / Et3N-3HF / acetonitrile / 12 h / 20 °C
10.1: 72 mg / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 0.33 h / 20 °C
11.1: 64 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 12 h / 20 °C
12.1: 90 percent / TFAA; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 1 h / 20 °C
With
pyridine; 2,4,6-trimethyl-pyridine; titanium(IV) isopropylate; sodium chlorite; sodium dihydrogenphosphate; triphenyl-arsane; 4 A molecular sieve; K-10 clay; lithium triethylborohydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; copper(l) chloride; tetramethylammonium triacetoxyborohydride;
tetrapropylammonium perruthennate; tris(dibenzylideneacetone)dipalladium (0);
In
tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol;
5.1: Stille cross-coupling / 12.1: Friedel-Crafts annulation;
DOI:10.1021/ja066621v