Multi-step reaction with 14 steps
1: 88 percent / BuLi / tetrahydrofuran / 0.83 h / -78 - 0 °C
2: 73 percent / LAH / tetrahydrofuran / 7.5 h / -78 - 0 °C
3: 93 percent / L-(+)-DET, TBHP, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH2Cl2 / 21 h / -25 °C
4: 94 percent / Ti(O-i-Pr)4 / CH2Cl2 / 2 h / Ambient temperature
5: 94 percent / NaOH, H2O / methanol / 0.75 h / Ambient temperature
6: 76 percent / pyridine / CH2Cl2 / 18 h / 0 °C
7: 100 percent / 2,6-lutidine / CH2Cl2 / 0.42 h / 0 °C
8: 98 percent / DIBAL / CH2Cl2 / 0.33 h / -78 °C
9: Dess-Martin periodinane / CH2Cl2 / 48 h
10: benzene / 21 h / Ambient temperature
11: 99 percent / DIBAL / CH2Cl2 / 0.33 h / -78 °C
12: 93 percent / D-(-)-DET, TBHP, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH2Cl2 / 21 h / -25 °C
13: 96 percent / diethyl ether / 23 h / -30 °C
14: 76 percent / Bu3P / CH2Cl2 / 4 h / Ambient temperature
With
pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; tributylphosphine; 4 A molecular sieve; water; diisobutylaluminium hydride; Dess-Martin periodane;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;
DOI:10.1055/s-1999-2689