Multi-step reaction with 11 steps
1.1: 92 percent / SnCl2 / diethyl ether / 3 h / 0 - 25 °C
2.1: 98 percent / K2CO3; MeOH / diethyl ether / 1 h / 25 °C
3.1: aq. NaIO4; NaHCO3 / methanol; CH2Cl2 / 2 h / 25 °C
4.1: 430 mg / iPr2NH; vinyl acetate / toluene / 12 h / 140 °C
5.1: 95 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C
6.1: 97 percent / Et3N; DMAP / CH2Cl2 / 2 h / 0 - 25 °C
7.1: 95 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 25 °C
8.1: 85 percent / Martin sulfurane; Et3N / CHCl3 / 2 h / 50 °C
9.1: 90 percent / K2CO3; MeOH / 6 h / 25 °C
10.1: NaH; 18-crown-6 / tetrahydrofuran / 0.25 h / 0 °C
10.2: 80 percent / tetrahydrofuran / 2 h / 0 °C
11.1: NMO; H2O; OsO4 / quinuclidine / acetone / 36 h / 25 °C
With
methanol; dmap; sodium periodate; osmium(VIII) oxide; vinyl acetate; N-methyl-2-indolinone; Martins sulfurane; 18-crown-6 ether; tetrabutyl ammonium fluoride; water; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; diisopropylamine; tin(ll) chloride;
Quinuclidine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; acetone; toluene;
1.1: Glycosidation / 2.1: Deacylation / 3.1: Oxidation / 4.1: Cyclization / 5.1: Silyl ether cleavage / 6.1: Esterification / 7.1: Silyl ether cleavage / 8.1: Dehydration / 9.1: Debenzoylation / 10.1: Metallation / 10.2: Etherification / 11.1: Oxidation;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8