Multi-step reaction with 10 steps
1.1: 97 percent / iPr2NEt / CH2Cl2 / 12 h / 40 °C
2.1: nBuLi / tetrahydrofuran; hexane; diethyl ether / 6 h / 25 °C
2.2: 85 percent / CuI / tetrahydrofuran; hexane; diethyl ether / -78 °C
3.1: SeO2 / ethanol / 0.5 h / Heating
3.2: 80 percent / NaBH4 / ethanol / 1 h / 0 °C
4.1: 88 percent / Ti(OiPr)4; D-(-)-diethyl tartrate; tBuOOH / CH2Cl2; toluene / 24 h / -24 °C
5.1: 95 percent / LiAlH4 / diethyl ether / 5 h / 25 °C
6.1: 95 percent / TsOH / 0.5 h / 25 °C
7.1: ammonium ceric nitrate / acetonitrile; H2O / 2 h / -5 °C
7.2: 1 mol/l HCl / methanol; H2O / 24 h / 25 °C
8.1: 80 percent / Red-Al / tetrahydrofuran / 1.5 h / 0 °C
9.1: 81 percent / Et3N; 4-dimethylaminopyridine / 4 h / 0 - 20 °C
10.1: 80 percent / N-bromosuccinimide; K2CO3; dibenzoyl peroxide / CCl4 / 9 h / Heating
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; selenium(IV) oxide; ammonium cerium(IV) nitrate; diethyl (2S,3S)-tartrate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; dibenzoyl peroxide;
In
tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; hexane; dichloromethane; water; toluene; acetonitrile;
1.1: Alkylation / 2.1: Metallation / 3.1: Oxidation / 4.1: Sharpless epoxidation / 5.1: Reduction / 6.1: Cyclization / 7.1: Oxidation / 7.2: cyclization / 8.1: Reduction / 9.1: Tosylation / 10.1: Bromination;
DOI:10.1002/1099-0690(200009)2000:18<3223::AID-EJOC3223>3.0.CO;2-L