Multi-step reaction with 11 steps
1: 80 percent / NaH / dimethylformamide / 48 h / 0 - 40 °C
2: 77 percent / Ph2PCH2CH2PPh2; Br2 / CH2Cl2 / 3.5 h / 0 - 20 °C
3: 83 percent / n-BuLi; CuI / tetrahydrofuran; hexane / 27 h / 35 °C
4: 8.5 mg / H2 / Lindlar catalyst / ethyl acetate; ethanol / 1.5 h
5: 97 percent / Na; naphthalene / 1,2-dimethoxy-ethane / -75 - 20 °C
6: 96 percent / tetrahydrofuran / 17 h / 20 °C
7: 82 percent / NaHSO4; LiOH / 1,2-dimethoxy-ethane; H2O / 8 h / 20 °C
8: 76 percent / DMAP; DCC / CH2Cl2 / 18 h / 20 °C
9: 80 percent / TBAF / tetrahydrofuran / 2 h
10: 82 percent / DMAP; DCC / CH2Cl2 / 4.5 h / 20 °C
11: 93 percent / morpholine; PPh3 / Pd(OAc)2 / tetrahydrofuran / 7 h
With
morpholine; dmap; lithium hydroxide; sodium hydrogen sulfate; copper(l) iodide; n-butyllithium; naphthalene; tetrabutyl ammonium fluoride; hydrogen; bromine; sodium; sodium hydride; dicyclohexyl-carbodiimide; triphenylphosphine; 1,2-bis-(diphenylphosphino)ethane;
palladium diacetate; Lindlar's catalyst;
In
tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo001200w