Multi-step reaction with 17 steps
1.1: 99 percent / K2CO3 / methanol
2.1: 86 percent / Et3N; DMAP
3.1: 85 percent / toluene / 48 h / Heating
4.1: 80 percent / 18-crown-6; oxone; aq. NaHCO3 / acetone; CH2Cl2 / 2 h / 0 °C
5.1: 81 percent / i-Pr2NEt / CH2Cl2 / 48 h / 20 °C
6.1: 92 percent / pyridine
7.1: 73 percent / TBAF
8.1: 79 percent / CSA
9.1: 89 percent / K2CO3 / methanol
10.1: 86 percent / i-Pr2NEt; NaI / CH2Cl2 / 18 h / Heating
11.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C
11.2: 2-benzenesulfonyl-3-(3-nitrophenyl)oxaziridine / tetrahydrofuran; toluene / 0.5 h / -78 °C
11.3: 74 percent / CSA / tetrahydrofuran; toluene / 1 h / -78 - 20 °C
12.1: 87 percent / CSA / CH2Cl2 / 18 h / 20 °C
13.1: 91 percent / toluene / 18 h / Heating
14.1: 88 percent / pyridine / CH2Cl2 / 1 h / 20 °C
15.1: 81 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C
With
pyridine; dmap; Oxone; 18-crown-6 ether; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene;
4.1: Claisen-Eschenmoser rearrangement;
DOI:10.1055/s-2004-834822