Multi-step reaction with 16 steps
1: Ph3P; DEAD / tetrahydrofuran / 0.5 h / 0 - 20 °C
2: K2CO3 / methanol / 0.5 h / 20 °C
3: 82 percent / Red-Al / diethyl ether / 3 h / 0 - 20 °C
4: 96 percent / Et2Zn / CH2Cl2 / 4 h / -20 - 0 °C
5: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 0.33 h / 0 - 20 °C
6: Zn(BH4)2 / tetrahydrofuran / 8 h / 0 °C
7: Et3N; DMAP / CH2Cl2 / 1 h / 0 - 20 °C
8: H2 / Pd/C / hexane / 1 h / 20 °C
9: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 0.33 h / 0 - 20 °C
10: diethyl ether / 1 h / 0 - 20 °C
11: (cHex)2BH / tetrahydrofuran / 1 h / 0 °C
12: H2O2; NaOH / H2O
13: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 0.33 h / 0 - 20 °C
14: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C
15: Et3N / tetrahydrofuran / 3 h / 20 °C
16: DMAP / toluene / 1 h / 20 °C
With
dmap; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; zinc(II) tetrahydroborate; 2-methyl-but-2-ene; bis(cyclohexanyl)borane; hydrogen; dihydrogen peroxide; diethylzinc; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; tert-butyl alcohol;
1: Mitsunobu reaction / 15: Yamaguchi esterification / 16: Yamaguchi esterification;
DOI:10.1016/j.tetlet.2006.08.055