Multi-step reaction with 9 steps
1.1: 95 percent / Et3N / diethyl ether / 1.5 h / 0 °C
2.1: 4 Angstroem molecular sieves / (1S,2R)-1-amino-2-indanol-derived tridentate Cr catalyst / 12 h / 20 °C
2.2: 80 percent / conc. HCl / CHCl3 / 4 h
3.1: 93 percent / NaBH4 / methanol / 1 h / 20 °C
4.1: 93 percent / 2,6-lutidine / CH2Cl2 / 3 h / -78 °C
5.1: 88 percent / 10-camphorsulfonic acid / CH2Cl2; methanol / 1 h / 20 °C
6.1: pyridine / CH2Cl2 / 1 h / -10 °C
7.1: LDA; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C
7.2: tetrahydrofuran; hexane / -78 - 20 °C
8.1: 85 mg / K2CO3 / methanol / 12 h / 20 °C
9.1: 86 percent / pyridinium p-toluenesulfonate; Hg(OAc)2; H2O / tetrahydrofuran / 1.5 h / 45 °C
With
pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; mercury(II) diacetate; water; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; lithium diisopropyl amide;
(1S,2R)-1-amino-2-indanol-derived tridentate Cr catalyst;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
2.1: hetero-Diels-Alder reaction;
DOI:10.1016/S0040-4020(03)00814-7