Multi-step reaction with 18 steps
1.1: 61 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C
2.1: 83 percent / NaBH4 / ethanol / 20 °C
3.1: 90 percent / acetic acid / 2 h / 80 °C
4.1: 99 percent / H2 / 10percent Pd/C / ethyl acetate / 6 h / 2482.38 Torr
5.1: 82 percent / LiAlH4 / diethyl ether / 24 h / Heating
6.1: 100 percent / DMAP / pyridine / 16 h / 20 °C
7.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8
8.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C
9.1: 100 percent / K2CO3 / methanol / 1.5 h / 20 °C
10.1: 100 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - -40 °C
11.1: 90 percent / NaOMe / methanol / 20 °C
12.1: 93 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C
13.1: 95 percent / 2-methyl-2-butene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 20 °C
14.1: CDI / tetrahydrofuran / 3 h / 20 °C
14.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C
15.1: CDI / tetrahydrofuran / 3 h / 20 °C
15.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C
16.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C
17.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C
17.2: 62 percent / benzene; CHCl3 / Heating
18.1: 47 percent / LDA; Py*HCl / tetrahydrofuran / -78 - 20 °C
With
1H-imidazole; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; pyridine hydrochloride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; lithium diisopropyl amide;
10percent Pd/C;
In
tetrahydrofuran; pyridine; methanol; phosphate buffer; diethyl ether; ethanol; hexane; dichloromethane; water; acetic acid; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
1.1: Formylation / 2.1: Reduction / 3.1: Cycloaddition / 4.1: Catalytic hydrogenation / 5.1: Reduction / 6.1: Acetylation / 7.1: Deacetylation / 8.1: silylation / 9.1: Deacetylation / 10.1: Oxidation / 11.1: Ring cleavage / 12.1: Alkylation / 13.1: Oxidation / 14.1: Substitution / 14.2: Substitution / 15.1: Substitution / 15.2: Substitution / 16.1: Grignard reaction / 17.1: desilylation / 17.2: lactonization / 18.1: epimerization;
DOI:10.1021/jo991582+