Multi-step reaction with 22 steps
1.1: 4.37 mg / aq. HCl / tetrahydrofuran; CH2Cl2 / 3 h / 20 °C
2.1: 96 percent / (S,S)-chiral titanium complex / diethyl ether; tetrahydrofuran / 5 h / -78 °C
3.1: 97 percent / KH / tetrahydrofuran / 0 - 20 °C
4.1: 98 percent / [1,3-Mes2-(N2C3H5)]Cl2(PCy3)Ru=CHPh; N-allyl-N-tritylamine; diisopropylethylamine / toluene / 3.5 h / Heating
5.1: OsO4; H2O; N-methylmorpholine N-oxide / acetone / 16 h / 20 °C
6.1: aq. NaIO4 / acetone / 2.5 h / 20 °C
7.1: 2.73 g / 4 Angstroem molecular sieves / toluene / 2.5 h / -78 - 0 °C
8.1: 92 percent / KH / tetrahydrofuran / 0 - 20 °C
9.1: OsO4; H2O; N-methylmorpholine N-oxide / acetone / 18 h / 20 °C
10.1: aq. NaIO4 / acetone / 2.5 h / 20 °C
11.1: s-BuLi / tetrahydrofuran; cyclohexane / 4.5 h / -78 - -20 °C
11.2: 1.18 g / citric acid / tetrahydrofuran; cyclohexane; H2O / pH 4 - 5
12.1: BF3*Et2O / tetrahydrofuran; cyclohexane / -78 - -5 °C
12.2: 1.49 g / ethanolamine / pentane / 2.5 h / 0 °C
13.1: 94 percent / 2,6-lutidine / CH2Cl2 / 10 h / -78 °C
14.1: 82 percent / NH4F; MeOH / 9.5 h / Heating
15.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 4 h
16.1: 54 percent / n-BuLi / diethyl ether; hexane / 1.5 h / -78 °C
17.1: 100 percent / NaH / dimethylformamide / 0 - 20 °C
18.1: 97 percent / N,N-dimethylbarbituric acid; Pd(PPh3)4 / CH2Cl2 / 2.5 h / Heating
19.1: 75 percent / Et3N; N,N-dimethylaminopyridine / tetrahydrofuran / 6 h / Heating
20.1: TBAF / tetrahydrofuran / 24 h / 20 °C
21.1: 89 percent / diisopropylethylamine / CH2Cl2 / 6 h / -78 °C
22.1: 72 percent / second generation Grubbs catalyst / toluene / 2 h / Heating
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; hydrogenchloride; methanol; dmap; ammonium fluoride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; 1,3-dimethylbarbituric acid; (S,S)-chiral titanium; [1,3-Mes2-(N2C3H5)]Cl2(PCy3)Ru=CHPh; 4 A molecular sieve; boron trifluoride diethyl etherate; N-tritylprop-2-en-1-amine; tetrabutyl ammonium fluoride; water; sec.-butyllithium; potassium hydride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; toluene;
11.1: Corey-Schlessinger olefination / 15.1: Dess-Martin oxidation;
DOI:10.1021/ol062642i