Multi-step reaction with 13 steps
1: 1.) Red-Al; 2.) I2 / 1.) Et2O, 0 deg C to 25 deg C; 2.) Et2O, -50 deg C to 25 deg C
2: PPTS / CH2Cl2
3: 1.) t-BuLi / 1.) Et2O, -78 deg C; 2.) DMF
4: DIBAH / CH2Cl2 / -78 °C
5: NaH, n-Bu4NI / tetrahydrofuran / Heating
6: PPTS / methanol / Heating
7: diisopropyl L-tartrate, Ti(O-i-Pr)4, t-BuOOH, 4 Angstroem molecular sieves / CH2Cl2 / -30 °C
8: CuI / tetrahydrofuran / -25 °C
9: PPTS / benzene / Heating
10: 1.) OsO4, NMO; 2.) NaIO4 / 1.) THF, H2O; 2.) THF, H2O
11: 80 percent / n-BuLi / tetrahydrofuran / 0 °C
12: Li / tetrahydrofuran; liquid ammonia / -33 °C
13: Et3N / CH2Cl2
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; L-(+)-diisopropyl tartrate; 4 A molecular sieve; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; diisobutylaluminium hydride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; methanol; dichloromethane; ammonia; benzene;
DOI:10.1016/S0040-4039(97)10754-7