Multi-step reaction with 12 steps
1.1: 82 percent / Jones reagent / acetone / 0 °C
2.1: LiAlH4; Darvon alcohol / -78 °C
3.1: 98 percent / DMAP; triethylamine / CH2Cl2 / 0 - 20 °C
4.1: lithium / tetrahydrofuran / 0 - 20 °C
4.2: CuCN / tetrahydrofuran / 0.5 h / 0 °C
4.3: 84 percent / tetrahydrofuran / -96 - -90 °C
5.1: 78 percent / diisobutylaluminum hydride / toluene; hexane / -78 - 0 °C
6.1: 1,3,5-trimethyl-benzene / Heating
7.1: tetrabutylammonium fluoride / tetrahydrofuran; 1,3,5-trimethyl-benzene / 1 h / 0 °C
8.1: 93 percent / H2; quinoline / Lindlar catalyst / methanol / 19 h / 20 °C
9.1: 74 percent / trimethylbenzylammonium chloride; triethylamine / P(PPh3)4 / acetonitrile / 48 h / 120 °C
10.1: 92 percent / DMAP; pyridine / 20 h / 100 °C
11.1: 1-pyrrolylborane
12.1: 96 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / -78 °C
With
pyridine; quinoline; dmap; lithium aluminium tetrahydride; jones reagent; 1-pyrrolylborane; Darvon alcohol; tetrabutyl ammonium fluoride; hydrogen; benzyltrimethylammonium chloride; lithium; sodium naphthalenide; diisobutylaluminium hydride; triethylamine;
Lindlar's catalyst; P(PPh3)4;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; acetone; toluene; acetonitrile; 1,3,5-trimethyl-benzene;
1.1: Oxidation / 2.1: Reduction / 3.1: Acetylation / 4.1: Metallation / 4.2: transmetalation / 4.3: silacupration / 5.1: Reduction / 6.1: imino ene cyclization / 7.1: desylilation / 8.1: Reduction / 9.1: Heck cyclization / 10.1: Tosylation / 11.1: hydroboration / 12.1: detosylation;
DOI:10.1021/ja970839n