Multi-step reaction with 8 steps
1.1: ozone / CH2Cl2 / 1 h / -78 °C
1.2: Ph3P / CH2Cl2 / 1.5 h / -78 - 20 °C
2.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 3 h / 20 °C
3.1: diethyl ether / 0 °C
4.1: NaH / 1,2-dimethoxy-ethane / 1.5 h / Heating
4.2: 48 percent / NaCl; H2O / dimethylsulfoxide / 1 h / 165 °C
5.1: LiHMDS / tetrahydrofuran / 0.75 h / -78 °C
5.2: tetrahydrofuran / 1 h / 0 °C
6.1: 8.82 g / PPh3; Et3N / Pd(OAc)2 / dimethylformamide / 20 °C
7.1: 26 percent / H2 / Pd/C / methanol / 72 h / atmospheric pressure
8.1: 79 percent / PPh3; ADDP / CH2Cl2 / 20 °C
With
sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydrogen; sodium hydride; ozone; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; 1,1'-azodicarbonyl-dipiperidine;
palladium diacetate; palladium on activated charcoal;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
4.1: Dieckmann condensation;
DOI:10.1016/j.ejmech.2004.02.010