Multi-step reaction with 20 steps
1.1: 85 percent / i-Pr2NEt / CH2Cl2 / 20 h / 25 °C
2.1: 80 percent / Li; liq. NH3 / 1 h / -78 °C
3.1: 99 percent / NaBH4 / tetrahydrofuran; ethanol / 3 h / -78 - 25 °C
4.1: 80 percent / imidazole; DMAP / dimethylformamide / 24 h / 25 °C
5.1: PPTS / acetone / 24 h / 65 °C
6.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C
7.1: 89 percent / PPh3; Pd(OAc)2; i-Pr2NEt / dimethylformamide / 12 h / 60 °C / 760 Torr
8.1: 95 percent / DIBAL-H / CH2Cl2 / 2 h / -78 - 0 °C
9.1: 65 percent / BH3*THF / tetrahydrofuran / 12 h / 0 °C
10.1: TEMPO; Br(OAc)2(1-)*Me3N(+)-resin / CH2Cl2 / 2 h / 25 °C
11.1: pyridine / CH2Cl2 / 0.1 h / 25 °C
12.1: NaClO2; 2-methyl-2-butene; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 25 °C
12.2: aq. HCl / dioxane / 16 h / 75 °C
13.1: 72 percent / 2,6-lutidine / CH2Cl2 / 1 h / 25 °C
14.1: 97 percent / Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 3 h / 25 °C
15.1: 78 percent / tetrahydrofuran / 12 h / 25 °C
16.1: 50 percent / SeO2; t-BuOOH / CH2Cl2 / 6 h / 25 °C
17.1: 57 percent / Br2; N,N-dimethylaniline / CH2Cl2 / 12 h / -78 - 0 °C
18.1: 75 percent / nBu3SnH; AIBN / toluene / 15 h / 110 °C
19.1: 90 percent / CSA / methanol / 1 h / 25 °C
20.1: 81 percent / Et3N; DMAP / CH2Cl2 / 12 h / 25 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; palladium diacetate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; selenium(IV) oxide; borane-THF; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); Br(OAc)2(1-)*Me3N(+)-resin; camphor-10-sulfonic acid; ammonia; bromine; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N,N-dimethyl-aniline; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
2.1: Birch reduction / 14.1: Dess-martin oxidation / 15.1: Wittig reaction;
DOI:10.1002/anie.200351744