Multi-step reaction with 14 steps
1.1: 97 percent / imidazole / CH2Cl2 / 20 °C
2.1: 76 percent / Et3N / 20 °C
3.1: 81 percent / aq. NaOH / methanol / 20 °C
4.1: SOCl2; pyridine / CH2Cl2 / 0 °C
5.1: NaN3 / acetone; H2O / 0 °C
6.1: toluene / Heating
7.1: n-BuLi / tetrahydrofuran / -78 - 20 °C
7.2: 67 percent / tetrahydrofuran / -78 °C
8.1: n-Bu4NF / tetrahydrofuran / 20 °C
9.1: DMAP; pyridine / CH2Cl2 / 20 °C
10.1: TFA / 20 °C
11.1: 64 percent / DMAP; pyridine / 50 °C
12.1: 92 percent / aq. NaOH / methanol; tetrahydrofuran / 20 °C
13.1: dimethylformamide / 80 °C
14.1: DIBAH / toluene / -78 - 20 °C
14.2: aq. NaOH / methanol; tetrahydrofuran / 20 °C
With
pyridine; 1H-imidazole; dmap; sodium hydroxide; n-butyllithium; thionyl chloride; sodium azide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
1.1: silylation / 2.1: Cycloaddition / 3.1: Hydrolysis / 4.1: Chlorination / 5.1: Substitution / 6.1: Rearrangement / 7.1: Metallation / 7.2: Condensation / 8.1: desilylation / 9.1: Acetylation / 10.1: acidolysis / 11.1: sulfonylation / 12.1: Deacetylation / 13.1: Substitution / 14.1: Reduction / 14.2: Hydrolysis;
DOI:10.1016/S0960-894X(00)00366-8