Multi-step reaction with 17 steps
1.1: triethylamine / CH2Cl2 / 1.5 h / 0 °C
2.1: 84 percent / DBU / 2 h / 80 °C
3.1: 47 percent / H2 / 10 percent Pd/C / ethanol / 4 h / 0 - 10 °C / 760 Torr
4.1: lithium perchlorate / diethyl ether / 168 h / 20 °C
5.1: 96 percent / H2 / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr
6.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C
7.1: 83 percent / DBU / toluene / 5 h / 100 °C
8.1: 96 percent / H2 / PtO2 / ethanol / 16 h / 20 °C / 760 Torr
9.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C
10.1: 1.50 g / BF3*Et2O / CH2Cl2 / 12 h / -60 °C
11.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
12.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C
12.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C
13.1: BH3*THF / tetrahydrofuran / 3 h / -78 °C
13.2: 73 percent / aq. NaOH; H2O2 / 0.5 h / 0 °C
14.1: triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 °C
15.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C
16.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH2Cl2 / 2 h / 20 °C
17.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / -78 °C
17.2: 100 percent / 1,2-dimethoxy-ethane; hexane / -78 °C
With
dmap; n-butyllithium; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane;
platinum(IV) oxide; palladium on activated charcoal;
In
tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene;
4.1: Diels-Alder reaction / 12.2: Wittig reaction / 17.2: Julia-Luthgoe reaction;
DOI:10.1016/S0040-4020(02)01358-3