Multi-step reaction with 14 steps
1.1: 51.92 g / TFA / dimethylformamide / 3 h / 45 °C
2.1: NaH / dimethylformamide / 0.08 h / 0 °C
2.2: 95 percent / nBu4NI / dimethylformamide / 2 h / 0 - 25 °C
3.1: 96 percent / PPTS; MeOH / 1 h / 25 °C
4.1: 91 percent / 2,6-lutidine / tetrahydrofuran / 0.5 h / -78 °C
5.1: 100 percent / DAST / CH2Cl2 / 0.5 h / 0 °C
6.1: 92 percent / SnCl2 / diethyl ether / 3 h / 0 - 25 °C
7.1: 98 percent / K2CO3; MeOH / diethyl ether / 1 h / 25 °C
8.1: 70 percent / TBAF / tetrahydrofuran / 0.25 h / 0 °C
9.1: aq. NaIO4; NaHCO3 / methanol; CH2Cl2 / 4 h / 25 °C
10.1: 95 mg / iPr2NH; vinyl acetate / toluene / 12 h / 140 °C
11.1: 65 percent / NMO; H2O; OsO4 / quinuclidine / acetone / 24 h / 25 °C
12.1: SOCl2; Ey3N / CH2Cl2 / 0.08 h / 0 °C
13.1: 62 mg / aq. NaIO4; NaHCO3 / acetonitrile; CCl4 / 1 h / 0 - 25 °C
14.1: 18-crown-6 / dimethylformamide / 1 h / 120 °C
14.2: 76 percent / aq. H2SO4 / tetrahydrofuran / 0.5 h / 0 °C
With
2,6-dimethylpyridine; methanol; sodium periodate; osmium(VIII) oxide; thionyl chloride; vinyl acetate; N-methyl-2-indolinone; 18-crown-6 ether; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; diisopropylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; trifluoroacetic acid; tin(ll) chloride;
Quinuclidine;
In
tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
1.1: Cyclization / 2.1: Metallation / 2.2: Etherification / 3.1: Ring cleavage / 4.1: Etherification / 5.1: Rearrangement / 6.1: Glycosidation / 7.1: Deacylation / 8.1: Silyl ether cleavage / 9.1: Oxidation / 10.1: Cyclization / 11.1: Oxidation / 12.1: Cyclization / 13.1: Oxidation / 14.1: Ring cleavage / 14.2: Hydrolysis;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8