Multi-step reaction with 20 steps
1: 86 percent / LiCl; iPr2NEt / acetonitrile / 12 h / 25 °C
2: 98 percent / LiAlH4; LiI / diethyl ether / 0.5 h / -100 °C
3: 97 percent / AcOH; H2O / 5 h / 25 °C
4: 70 percent / N-iodosuccinimide; NaHCO3 / tetrahydrofuran / 2.5 h / 0 °C
5: 90 percent / Et3N; 4-DMAP / CH2Cl2 / 3 h / -10 - 0 °C
6: 100 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -10 °C
7: 99 percent / H2 / Raney Ni / ethanol / 1 h / 25 °C
8: 88 percent / H2 / Pd(OH)2/C / ethanol / 3 h / 25 °C
9: 99 percent / Dess Martin periodinane / CH2Cl2 / 2 h / 25 °C
10: 87 percent / tetrahydrofuran / 3 h / -78 - -10 °C
11: 95 percent / Dess Martin periodinane / CH2Cl2 / 3 h / 25 °C
12: 98 percent / triethyl orthoformate; pTsOH / 55 °C
13: OsO4; H2O; N-methylmorpholine / 2-methyl-propan-2-ol; tetrahydrofuran / 14 h / 25 °C
14: NaIO4; H2O / 5 h / 25 °C / pH 7
15: 87 percent / nBuLi / hexane; tetrahydrofuran / 0.67 h / -20 °C
16: 88 percent / Dess Martin periodinane / CH2Cl2 / 1 h / 25 °C
17: 85 percent / TMSOTf / CH2Cl2 / 1 h / -78 - -30 °C
18: 93 percent / pyridine / 2 h / 25 °C
19: 91 percent / NBS; 2,6-lutidine / acetonitrile; H2O / 2 h / 25 °C
20: 92 percent / NaBH4 / methanol / 0.08 h / -5 °C
With
4-methyl-morpholine; pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; N-iodo-succinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; water; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; orthoformic acid triethyl ester; lithium chloride; lithium iodide;
palladium dihydroxide; nickel;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol;
9: Dess-Martin oxidation / 11: Dess-Martin oxidation / 16: Dess-Martin oxidation;
DOI:10.1002/1521-3773(20011105)40