Multi-step reaction with 11 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: 0.71 g / SnCl2 / diethyl ether / 3 h / 0 - 25 °C
6.1: 99 percent / NaOH / methanol / 1 h / 25 °C
7.1: aq. NaIO4 / NaHCO3 / CH2Cl2; methanol / 2 h / 25 °C
8.1: 0.120 g / iPr2NH; vinyl acetate / toluene / 16 h / 140 °C
9.1: 98 percent / TBAF / tetrahydrofuran / 1 h / 25 °C
10.1: 97 percent / Et3N / CH2Cl2 / 2 h / 0 - 25 °C
11.1: 87 percent / DBU / toluene / 24 h / Heating
With
2,6-dimethylpyridine; methanol; sodium hydroxide; sodium periodate; vinyl acetate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride;
sodium hydrogencarbonate;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
1.1: Metallation / 1.2: Etherification / 2.1: Ring cleavage / 3.1: Etherification / 4.1: Rearrangement / 5.1: Glycosidation / 6.1: Debenzoylation / 7.1: Oxidation / 8.1: Cyclization / 9.1: Silyl ether cleavage / 10.1: Mesylation / 11.1: Elimination;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8