Multi-step reaction with 7 steps
1.1: LDA / tetrahydrofuran / 0.17 h / -110 °C
1.2: 82 percent / tetrahydrofuran
2.1: KOtBu / tetrahydrofuran / 0.25 h / 0 °C
2.2: 86 percent / AD-mix α; MeSO2NH2 / tetrahydrofuran; H2O; 2-methyl-propan-2-ol
3.1: 83 percent / iPrNEt2; 4-DMAP / CH2Cl2 / 40 °C
4.1: dibal-H / CH2Cl2; toluene / -78 - 20 °C
4.2: resin-CH2-N(Me)3(+)*Br(OAc)2(-); TEMPO / CH2Cl2 / 2 h / 50 °C
5.1: tBuLi; MgBr2*Et2O / diethyl ether; pentane / -78 °C
5.2: diethyl ether; pentane / 0.5 h
5.3: 62 percent / Bu4NI; NaH / 8 h / 70 °C
6.1: 85 percent / CSA / CH2Cl2 / 20 °C
7.1: 96 percent / resin-CH2-N(Me)3(+)*Br(OAc)2(-); TEMPO / CH2Cl2 / 2 h / 50 °C
With
dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N,N-diethyl-N-isopropylamine; resin-CH2-N(Me)3(+)*Br(OAc)2(-); camphor-10-sulfonic acid; potassium tert-butylate; tert.-butyl lithium; diisobutylaluminium hydride; magnesium bromide; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene; pentane;
DOI:10.1016/j.tetlet.2004.04.056