Multi-step reaction with 10 steps
1: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C
2: 91 percent / pyridine / 4 h / 0 °C
3: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h
5: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h
6: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature
7: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature
8: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature
9: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature
10: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h
With
methanol; tert.-butylhydroperoxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese(IV) oxide; Montmorillonite; n-butyllithium; oxalyl dichloride; Ti(i-PrO); potassium tert-butylate; water; hydrogen; diisobutylaluminium hydride; magnesium sulfate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
Lindlar's catalyst;
In
tetrahydrofuran; pyridine; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene;
DOI:10.1002/hlca.19880710502