Multi-step reaction with 9 steps
1: 1.) NaH / 1.) DME, MeOH, reflux, 10 min, 2.) DME, MeOH, reflux, overnight
2: (S)-BINAP-RuCl2, AcOH, H2 / methanol
3: 99 percent / imidazole / CH2Cl2 / Ambient temperature
4: 76 percent / DIBAL-H, methyl (1S(1α,2α,3aβ,7aα))-2-tert-butyldimethylsilyloxyindan-1-carboxylate / CH2Cl2 / 1.25 h / -78 °C
5: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, -50 deg C -> room temperature, 5 h
6: 553 mg / K2CO3 / methanol / 0 deg C -room temperature, overnight
7: 95 percent / Dowex-50 sulfonic acid resin / methanol / Ambient temperature
8: 1.) AIBN, Bu3SnH, 2.) I2 / 1.) toluene, 100 - 105 deg C - 3 h, room temperature - overnight, 2.) Et2O, 30 min
9: 82 percent / Ph3P, DEAD / benzene / 14 h / Ambient temperature
With
1H-imidazole; oxalyl dichloride; dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II); 2,2'-azobis(isobutyronitrile); Dowex-50 sulfonic acid resin; methyl (1S(1α,2α,3aβ,7aα))-2-tert-butyldimethylsilyloxyindan-1-carboxylate; hydrogen; iodine; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate;
In
methanol; dichloromethane; benzene;
DOI:10.1021/ja962162u