Multi-step reaction with 17 steps
1.1: 73 percent / DIBALH / CH2Cl2 / 0.67 h / -78 °C
2.1: (+)-diisopropyl tartrate; Ti(OiPr)4; TBHP / 4A MS / CH2Cl2 / 12 h / -30 °C
3.1: 100 percent / LiAlH4 / tetrahydrofuran / 1 h / 24 °C
4.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0.75 h / -40 °C
5.1: 89 percent / K2CO3 / methanol / 0.03 h / 23 °C
6.1: 87 percent / TPAP; NMO; 4A MS / CH2Cl2 / 0.5 h / 0 °C
7.1: NaH / benzene; tetrahydrofuran / 0.08 h / 0 °C
7.2: 85 percent / benzene; tetrahydrofuran / 8 h / -78 °C
8.1: 98 percent / NaBH4; CeCl3*H2O / ethanol / 3 h / -20 °C
9.1: 93 percent / K2CO3 / methanol / 2 h / 24 °C
10.1: 95 percent / m-CPBA; NaHCO3 / CH2Cl2 / 2 h / 0 °C
11.1: 2,6-lutidine / CH2Cl2 / 1 h / -20 °C
12.1: 77 percent / CSA / CH2Cl2 / 4 h / 0 °C
13.1: 95 percent / pyridine / CH2Cl2 / 2 h / 0 °C
14.1: 95 percent / TMSOTf; 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
15.1: 94 percent / Bu3P / CH2Cl2 / 1 h / 25 °C
16.1: 100 percent / LiAlH4 / diethyl ether / 1.5 h / -30 °C
17.1: 93 percent / 2,6-lutidine / CH2Cl2 / 3 h / -30 °C
With
pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium tetrahydride; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; L-(+)-diisopropyl tartrate; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid;
4A MS;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; benzene;
2.1: Katsuki-Sharpless asymmetric epoxidation / 7.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tetlet.2007.04.136