Multi-step reaction with 15 steps
1.1: NaH / dimethylformamide / 0.08 h / 0 °C
1.2: 95 percent / nBu4NI / dimethylformamide / 2 h / 0 - 25 °C
2.1: 96 percent / PPTS; MeOH / 1 h / 25 °C
3.1: 91 percent / 2,6-lutidine / tetrahydrofuran / 0.5 h / -78 °C
4.1: 100 percent / DAST / CH2Cl2 / 0.5 h / 0 °C
5.1: 92 percent / SnCl2 / diethyl ether / 3 h / 0 - 25 °C
6.1: 98 percent / K2CO3; MeOH / diethyl ether / 1 h / 25 °C
7.1: aq. NaIO4; NaHCO3 / methanol; CH2Cl2 / 2 h / 25 °C
8.1: 430 mg / iPr2NH; vinyl acetate / toluene / 12 h / 140 °C
9.1: 95 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C
10.1: 97 percent / Et3N; DMAP / CH2Cl2 / 2 h / 0 - 25 °C
11.1: 95 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 25 °C
12.1: 85 percent / Martin sulfurane; Et3N / CHCl3 / 2 h / 50 °C
13.1: NMO; H2O; OsO4 / quinuclidine / acetone; 2-methyl-propan-2-ol / 24 h / 25 °C
14.1: 98 percent / K2CO3; MeOH / 4 h / 25 °C
15.1: 96 percent / pyridine / CH2Cl2 / 1 h / -78 - 25 °C
With
pyridine; 2,6-dimethylpyridine; methanol; dmap; sodium periodate; osmium(VIII) oxide; vinyl acetate; N-methyl-2-indolinone; Martins sulfurane; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; diisopropylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride;
Quinuclidine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
1.1: Metallation / 1.2: Etherification / 2.1: Ring cleavage / 3.1: Etherification / 4.1: Rearrangement / 5.1: Glycosidation / 6.1: Deacylation / 7.1: Oxidation / 8.1: Cyclization / 9.1: Silyl ether cleavage / 10.1: Esterification / 11.1: Silyl ether cleavage / 12.1: Dehydration / 13.1: Oxidation / 14.1: Debenzoylation / 15.1: Cyclization;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8