Multi-step reaction with 18 steps
1.1: 70 g / K2CO3; CH3SO2NH2; quinuclidine / K2Os2O2(OH)4; K3Fe(CN)6 / 2-methyl-propan-2-ol; H2O / 6 h / 20 °C
2.1: 43.8 g / NaIO4 / tetrahydrofuran; H2O / 2 h / 0 - 20 °C
3.1: 26.8 g / NaBH4; MeOH / tetrahydrofuran / 3 h / cooling
4.1: AgOTf; Na2CO3; 2,6-lutidine / CH2Cl2 / 0.33 h / cooling
4.2: CH2Cl2 / 16.5 h / -78 - 20 °C
4.3: 10.0 g / toluene / 14 h / 20 °C
5.1: 53 percent / NaHCO3 / xylene / 114 h / Heating
6.1: 7.7 g / mCPBA; NaH2PO4*H2O / CH2Cl2 / 21 h / 0 - 20 °C
7.1: 84 percent / DBU / tetrahydrofuran / 20 h / 20 °C
8.1: 100 percent / TFA / 0.5 h / 20 °C
9.1: ethyl chloroformate; triethylamine / CH2Cl2 / 0.5 h / cooling
9.2: 100 percent / NaBH4; MeOH / tetrahydrofuran / 1.17 h / -40 - 0 °C
10.1: 4.0 g / DMAP; triethylamine / CH2Cl2 / 17 h / 0 - 20 °C
11.1: 84 percent / iPr2NEt; DMAP / CH2Cl2 / 26 h / 20 - 40 °C
12.1: 92 percent / Zn-Ag couple; NaHCO3 / methanol / 18 h / Heating
13.1: 69 percent / xylene / 5 h / Heating; ambient pressure
14.1: 86 percent / pyridinium p-toluenesulfonate / methanol / 14 h / Heating
15.1: 0.14 g / HMPA; NaN(TMS)2 / tetrahydrofuran; toluene / 18 h / -78 - 20 °C
16.1: 0.060 g / MeOH / benzene; petroleum ether / 0.5 h / 0 - 20 °C
17.1: 92 percent / DMP / CH2Cl2 / 1.17 h / 0 - 20 °C
With
Quinuclidine; 2,6-dimethylpyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; methanesulfonamide; phthalic acid dimethyl ester; silver trifluoromethanesulfonate; silver; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; chloroformic acid ethyl ester; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; zinc;
potassium osmate; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; xylene; Petroleum ether; tert-butyl alcohol; benzene;
5.1: intramolecular Diels-Alder reactiom / 15.1: Dieckmann condensation;
DOI:10.1021/ja0581346