Multi-step reaction with 10 steps
1.1: aq. AcOH / tetrahydrofuran / 12 h / 23 °C
2.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 2 h / 23 °C
3.1: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 23 °C
4.1: benzene; methanol / 1 h / 23 °C
5.1: TiCl4 / CH2Cl2 / 0.5 h / -78 °C
5.2: DIPEA / CH2Cl2 / 3 h / -78 °C
5.3: CH2Cl2 / 48 h / -78 °C
6.1: aq. LiOH / tetrahydrofuran / 12 h / 23 °C
7.1: DIPEA / acetone / 1.5 h / 0 °C
8.1: aq. NaN3 / acetone / 1.5 h / 0 °C
9.1: toluene / 2 h / Heating
10.1: toluene / 18 h / 70 °C
With
lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; sodium azide; 2-methyl-but-2-ene; titanium tetrachloride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; dichloromethane; acetone; toluene; tert-butyl alcohol; benzene;
2.1: Dess-Martin oxidation / 9.1: Curtius rearrangement;
DOI:10.1016/j.bmcl.2004.08.045