Multi-step reaction with 12 steps
1.1: O2; rose bengal; AcONa / methanol / 1.33 h / -78 °C
1.2: 35 percent / (NH2)2CS / methanol / 13 h / 20 °C
2.1: 94 percent / lipase AK / tetrahydrofuran / 7 h / 20 °C
3.1: 87 percent / Ag2O; KI / toluene / 15.5 h / 20 °C
4.1: NaIO4; KMnO4; Na2CO3 / acetone; H2O / 1 h / 20 °C
5.1: NMM / 1,2-dimethoxy-ethane / 3 h / 20 °C
6.1: NaBH4 / 0.17 h / 0 °C
7.1: PhOCSCl; DMAP / CH2Cl2 / 4 h / 20 °C
7.2: 46 percent / AIBN; n-Bu3SnH / toluene / 1 h / 75 °C
8.1: NaOH / methanol / 1 h / 20 °C
8.2: 85 percent / H(+) / methanol / pH 6 - 7
9.1: K2CO3 / acetone / 3.5 h / 20 °C
10.1: BF3*Et2O / cyclopentane / 2 h / 20 °C
11.1: K2CO3 / methanol / 2 h / Heating
12.1: 57 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; N-methylmorpholine; 1-hydroxybenzotriazole / dimethylformamide / 6 h / 20 °C
With
4-methyl-morpholine; dmap; sodium hydroxide; sodium tetrahydroborate; potassium permanganate; sodium periodate; lipase AK; boron trifluoride diethyl etherate; oxygen; sodium acetate; rose bengal; sodium carbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; phenylcarbonochloridothioate; potassium iodide; silver(l) oxide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; Cyclopentane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/S0040-4039(01)00649-9