Multi-step reaction with 17 steps
1: porcine pancreatic lipase on celite
2: (COCl)2, DMSO, Et3N / CH2Cl2 / -78 - 25 °C
3: n-BuLi / tetrahydrofuran / 0 °C
4: 3N NaOH, Bu4NOH / H2O; tetrahydrofuran / 60 °C
5: (COCl)2, DMSO, Et3N / CH2Cl2 / -78 - 25 °C
6: CH2Cl2
7: 98 percent / H2O2, DHP / tetrahydrofuran
8: 1.) O3; 2.) PPh3 / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C -> 25 deg C
9: 90 percent / toluene; tetrahydrofuran / -78 °C
10: 88 percent / Zn, H2O / methanol
11: 99 percent / NaH / tetrahydrofuran
12: 1.) O3; 2.) PPh3 / 1.) CH2Cl2, -78 deg C; 2.) CH2Cl2, -78 --> 25 deg C
13: 49 percent / CrCl2, NiCl2, DMSO
14: 75 percent / NaH, NaI / tetrahydrofuran / 0 - 25 °C
15: 84 percent / Amberlyst 15 / methanol
16: 85 percent / Bu3P / benzene
17: 93 percent / Oxone, pH4 buffer, / tetrahydrofuran; methanol
With
3,4-dihydro-2H-pyran; chromium dichloride; Oxone; sodium hydroxide; n-butyllithium; Amberlyst 15; oxalyl dichloride; tributylphosphine; pH4 buffer; porcine pancreatic lipase on Celite; tetra(n-butyl)ammonium hydroxide; water; dihydrogen peroxide; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium iodide; nickel dichloride; zinc;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; benzene;
DOI:10.1016/S0040-4039(00)73057-7