Multi-step reaction with 9 steps
1.1: (i-Pr)2NLi / tetrahydrofuran / 0.5 h / -78 °C
1.2: tetrahydrofuran / 3.5 h / -78 - -40 °C
2.1: LDA / tetrahydrofuran / 1 h / -78 °C
2.2: 70 percent / Na2SO4; H2O / tetrahydrofuran / -78 - 0 °C
3.1: 87 percent / HCl / methanol / 2 h / 20 °C
4.1: 91 percent / Et3N; DMAP / CH2Cl2 / 14 h / 20 °C
5.1: 82 percent / NaN3 / dimethylformamide / 5 h / 65 °C
6.1: 70 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating
7.1: 93 percent / diethyl ether
8.1: 90 percent / H2 / Pd/C / methanol / 760.05 Torr
9.1: 72 percent / EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C
With
hydrogenchloride; dmap; sodium azide; hydrogen; trimethylaluminum; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
1.1: Alkylation / 1.2: Alkylation / 2.1: Isomerization / 2.2: Hydrolysis / 3.1: Hydrolysis / 4.1: Tosylation / 5.1: Substitution / 6.1: Ring cleavage / 7.1: Esterification / 8.1: Reduction / 9.1: Condensation;
DOI:10.1021/jo991288h