Multi-step reaction with 16 steps
1: 87 percent / H2 / Pd(OH)2/C / ethyl acetate
2: Et3N / 1,2-dichloro-ethane / -15 °C
3: BuLi / tetrahydrofuran; various solvent(s) / -78 °C
4: PPTS / propan-1-ol
5: Red-Al / diethyl ether
6: 97 percent / (D)-(-)-diethyl tartrate, Ti(O(i-Pr))4, t-BuOOH, 4 Angstroem molecular sieves / CH2Cl2 / -20 °C
7: SO3-pyridine, Et3N, DMSO / 1,2-dichloro-ethane
8: toluene
9: Bu4NF / tetrahydrofuran
10: Pd(PPh3)4, PPh3 / CH2Cl2 / 0.08 h
11: 98 percent / DIBAL-H / CH2Cl2 / -78 °C
12: 92 percent / NaH / dimethylformamide; tetrahydrofuran / 0 °C
13: p-MeC6H4SO3H*H2O / methanol
14: PPTS / 1,2-dichloro-ethane
15: 97 percent / DIBAL-H / CH2Cl2 / -40 °C
16: Et3N / CH2Cl2 / 0 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; pyridine-SO3 complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
palladium dihydroxide; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine;
In
tetrahydrofuran; methanol; propan-1-ol; diethyl ether; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1039/a702158e