Multi-step reaction with 17 steps
1: Na, NH3 / diethyl ether
2: PPTS / CH2Cl2
3: Et3N / CH2Cl2 / -5 °C
4: NaI, molecular sieves 4 Angstroem / butan-2-one / 45 °C
5: 1.) BuLi, DMPU / 1.) THF, -78 deg C, 2.) THF
6: CSA / methanol
7: TPAP, NMO, molecular sieves 4 Angstroem / CH2Cl2
8: Ph3P / 0 °C
9: BuLi
10: 1.) BuLi, Me2AlCl / 1.) PhMe, 0 deg C; CH2Cl2, 0 deg C to r.t., 2.) PhMe, CH2Cl2
11: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) THF, reflux, 2.) THF, H2O2, r.t.
12: NaBH4 / ethanol / 0 °C
13: 95 percent / 2,6-lutidine / CH2Cl2
14: 95 percent / H2 / Pd/C / methanol; CH2Cl2
15: 97 percent / TPAP, NMO, molecular sieves 4 Angstroem / CH2Cl2
16: 90 percent / toluene / Heating
17: 98 percent / CAN, H2O / acetonitrile; tetrahydrofuran / 0 °C
With
2,6-dimethylpyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; ammonium cerium(IV) nitrate; 4 A molecular sieve; camphor-10-sulfonic acid; ammonia; water; hydrogen; dihydrogen peroxide; sodium; dimethylaluminum chloride; pyridinium p-toluenesulfonate; triethylamine; triphenylphosphine; sodium iodide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; acetonitrile; butanone;